Dihalopropene compounds, insecticidal/acaricidal agents containing same, and intermediates for their production

ABSTRACT

The dihalopropene compounds of the general formula [I] have excellent insecticidal/acaricidal activity, so that they are satisfactorily effective for the control of noxious insects, mites and ticks.

This application is a continuation of application Ser. No. 08/624,488 filed on Apr. 4, 1996, now abandoned.

This is the U.S. National stage Application of PCT/JP95/01439 filed Jul. 20, 1995 now WO96/04228 published Feb. 15, 1996.

1. Technical Field

The present invention relates to dihalopropene compounds, insecticidal/acaricidal agents containing these compounds as active ingredients, for their production.

2. Background Art

As disclosed in JP-A 48-86835/1973 and JP-A 49-1526/1974, for example, it is well known that some kinds of propene compounds can be used as an active ingredient of insecticides.

In view of their insecticidal/acaricidal activity, it cannot always be said that these compounds are satisfactorily active for the control of noxious insects, mites and ticks.

Disclosure of Invention

The present inventors have intensively studied to find a compound having excellent insecticidal/acaricidal activity. As a result, they have found that particular dihalopropene compounds have satisfactory insecticidal/acaricidal activity for the control of noxious insects, mites and ticks, thereby completing the present invention.

That is, the present invention provides a dihalopropene compound (hereinafter referred to as the present compound) of the general formula: ##STR1## wherein R¹ is C₁ -C₁₀ alkyl, C₁ -C₅ haloalkyl, C₂ -C₁₀ alkenyl, C₂ -C₆ haloalkenyl, C₃ -C₉ alkynyl, C₃ -C₅ haloalkynyl, C₂ -C₇ alkoxyalkyl, (C₁ -C₃) alkoxy (C₁ -C₇) carbonylalkyl, C₂ -C₇ alkylthioalkyl; C₃ -C₆ cycloalkyl which may be substituted with C₁ -C₄ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; C₄ -C₉ cycloalkylalkyl which may be substituted with C₁ -C₄ alkyl; C₅ -C₆ cycloalkenyl which may be substituted with C₁ -C₄ alkyl; C₆ -C₈ cycloalkenylalkyl which may be substituted with C₁ -C₄ alkyl; or Q₁, Q₂, Q₃, Q₄, Q₅, Q₆, Q₇, Q₈, Q₉ or Q₁₀ of the general formula: ##STR2## wherein R⁴ and R¹² are independently halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy,

R⁵ and R⁶ are independently hydrogen, C₁ -C₃ alkyl, trifluoromethyl or halogen,

R⁷ is hydrogen or C₁ -C₃ alkyl,

R⁸ is hydrogen, halogen or methyl,

R⁹ is halogen, cyano, nitro, hydroxy, pentafluorosulfanyl(F₅ S), C₁ -C₈ alkyl, C₁ -C₃ haloalkyl, C₁ -C₈ alkoxy, haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio, C₃ -C₆ alkenyloxy, C₃ -C₆ haloalkenyloxy, C₁ -C₃ hydroxyalkyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl, C₂ -C₄ alkynyloxy, C₂ -C₄ haloalkynyl, C₂ -C₄ haloalkynyloxy, C₂ -C₄ alkoxyalkyl, C₂ -C₄ alkylthioalkyl, C₃ -C₆ cycloalkyl, C₅ -C₆ cycloalkenyl, C₂ -C₅ alkoxycarbonyl, C₃ -C₆ cycloalkyloxy, C₅ -C₆ cycloalkenyloxy; phenyl which may be substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, C₃ -C₆ alkenyloxy or C₃ -C₆ haloalkenyloxy; phenoxy which may be substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, C₃ -C₆ alkenyloxy or C₃ -C₆ haloalkenyloxy; benzyl which may be substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, C₃ -C₆ alkenyloxy or C₃ -C₆ haloalkenyloxy; benzyloxy which may be substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, C₃ -C₆ alkenyloxy or C₃ -C₆ haloalkenyloxy; or pyridyloxy which may be substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, C₃ -C₆ alkenyloxy or C₃ -C₆ haloalkenyloxy; or

when l is an integer of 2 to 5, two adjacent R⁹ 's are taken together to form trimethylene, tetramethylene, methylenedioxy which may be substituted with halogen or C₁ -C₃ alkyl; or ethylenedioxy which may be substituted with halogen or C₁ -C₃ alkyl,

R¹⁰, R¹¹, R¹⁵ and R¹⁶ are independently hydrogen, C₁ -C₃ alkyl or trifluoromethyl,

A is oxygen, S(O)_(t), NR¹³, C(═G¹)G² or G¹ C(═G²) wherein G¹ and G² are independently oxygen or sulfur, R¹³ is hydrogen, acetyl or C₁ -C₃ alkyl, and t is an integer of 0 to 2,

Z¹ is oxygen, sulfur or NR¹⁷ wherein R¹⁷ is hydrogen, acetyl or C₁ -C₃ alkyl,

l is an integer of 0 to 5,

m is an integer of 0 to 4,

n is an integer of 1 or 2,

p is an integer of 0 to 6,

q is an integer of 0 to 3, and

s is an integer of 1 to 6,

R², R³ and R¹⁴ are independently halogen, C₁ -C₃ haloalkyl or C₁ -C₃ alkyl,

r is an integer of 0 to 2,

X's are independently chlorine or bromine,

Y is oxygen, NH or sulfur, and

Z is oxygen, sulfur or NR¹³ wherein R¹³ is hydrogen, acetyl or C₁ -C₃ alkyl.

The present invention also provides an insecticidal/acaricidal agent containing the above dihalopropene compound as an active ingredient.

The present invention further provides the following compounds which are useful as intermediates for producing some of the present compounds:

a compound of the general formula: ##STR3## wherein R² and R³ are independently halogen, C₁ -C₃ alkyl or C₁ -C₃ haloalkyl, R⁷ is hydrogen or C₁ -C₃ alkyl, R¹⁰ and R¹¹ are independently hydrogen, C₁ -C₃ alkyl or trifluoromethyl, X's are independently chlorine or bromine, L¹ is hydroxy, halogen, methanesulfonyloxy or p-toluenesulfonyloxy, and e is an integer of 2 to 4; and particularly, a compound wherein R⁷, R¹⁰ and R¹¹ are all hydrogen, and e is 2 or 3;

a compound of the general formula: ##STR4## wherein R² and R³ are independently halogen, C₁ -C₃ alkyl or C₁ -C₃ haloalkyl, and X's are independently chlorine or bromine;

a compound of the general formula: ##STR5## wherein R²¹ and R²² are independently halogen or C₁ -C₃ alkyl, R¹⁹ is halogen, C₁ -C₃ haloalkoxy or trifluoromethyl, u is 1 to 4, and l is an integer of 0 to 5;

a compound of the general formula: ##STR6## wherein R² and R³ are independently halogen, C₁ -C₃ alkyl or C₁ -C₃ haloalkyl, R⁷ is hydrogen or C₁ -C₃ alkyl, R¹⁰ and R¹¹ are independently hydrogen, C₁ -C₃ alkyl or trifluoromethyl, R²⁰ is halogen, C₁ -C₃ alkoxy, trifluoromethyl or C₁ -C₃ haloalkoxy, l is an integer of 0 to 5, and e is an integer of 1 to 4; and particularly, a compound wherein B is oxygen; a compound wherein R² and R³ are independently halogen or C₁ -C₃ alkyl, R⁷, R¹⁰ and R¹¹ are all hydrogen, e is 1 to 4, and B is oxygen, S(O)_(t) or NR¹³ wherein R¹³ is hydrogen, acetyl or C₁ -C₃ alkyl, and t is an integer of 0 to 2.

DETAILED DESCRIPTION OF THE INVENTION

The variables in the above formulae for the present compounds and their intermediates can take the following specific examples.

Examples of the halogen atom represented by R², R³, R⁴, R⁵, R⁶, R⁸, R⁹ or R¹² or present in R⁹ are fluorine, chlorine, bromine or iodine.

Examples of the C₁ -C₁₀ alkyl group represented by R¹ are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, n-heptyl, isohexyl, n-octyl, n-nonyl, n-decyl, 3-n-pentyl, 2-ethylbutyl, 1-methylpentyl, 1-ethylbutyl, 3-methylpentyl, 1,3-dimethylbutyl, 1-methylheptyl and 1-methyloctyl.

Examples of the C₁ -C₄ alkyl group present in R¹ or R⁹, or represented by R⁴ or R¹², are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

Examples of the C₁ -C₃ alkyl group represented by R², R³, R⁵, R⁶, R⁷, R¹⁰, R¹¹, R¹³, R¹⁴, R¹⁵ or R¹⁶ are methyl, ethyl, n-propyl and isopropyl.

Examples of the C₁ -C₈ alkyl group represented by R⁹ are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethylpropyl, n-hexyl, isohexyl, 2-ethylbutyl, 1-methylpentyl, 1-ethylbutyl, 3-methylpentyl, 1,3-dimethylbutyl, n-heptyl, n-octyl and 1-methylheptyl.

Examples of the C₁ -C₅ haloalkyl group represented by R¹ are trifluoromethyl, difluoromethyl, bromodifluoromethyl, 2,2,2-trifluoroethyl, perfluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-dichloroethyl, 2-bromo-1,1,2,2-tetrafluoroethyl, 1,1,2,2,-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-bromo-1,1,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 3-chloropropyl, 3-bromopropyl, 3-fluoropropyl, 3-iodopropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, 2-chloropropyl, 1-chloro-1-methylethyl, 1-bromo-1-methylethyl, 2-fluoro-1-(fluoromethyl)ethyl, 2-chloro-1-(chloromethyl)ethyl, 2-bromo-1-(bromomethyl)ethyl, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl, 2,3-dibromopropyl, 4-fluorobutyl, 4-bromobutyl, 4-chlorobutyl, 4-iodobutyl, 4-(bromomethyl)propyl, 3-chloro-2,2-dimethyl-n-propyl, 3-bromo-2,2-dimethylpropyl, 2,2,3,4,4,4-hexafluorobutyl, 3-bromo-1-(bromomethyl)propyl and 2,2,3,3,4,4,5,5-octafluoropentyl.

Examples of the C₁ -C₃ haloalkyl group presented by R², R³, R⁴, R⁹ and R¹⁴, or present in R⁹, are trifluoromethyl, difluoromethyl, bromodifluoromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, 2,2,3,3,3-pentafluoropropyl, 3,3,3-trifluoropropyl, 1-fluoropropyl, 2-chloropropyl and 3-bromopropyl.

Examples of the C₂ -C₁₀ alkenyl group represented by R¹ are vinyl, allyl, homoallyl, isopropenyl, 2-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 3-methyl-3-butenyl, 1-ethyl-2-propenyl, 2-ethyl-2-propenyl, 2-pentenyl, 2-methyl-2-butenyl, 1-methyl-2-butenyl, 2-methyl-3-butenyl, 4-pentenyl, 1-methyl-3-butenyl, 1-ethyl-2-propenyl, 1-propyl-2-propenyl, 3-hexenyl, 2-isopropyl-2-propenyl, 2-ethyl-2-butenyl, 2-methyl-2-pentenyl, 1-ethyl-2-butenyl, 1-methyl-4-pentenyl, 1,3-dimethyl-2-butenyl, 2-hexenyl, 4-hexenyl, 5-hexenyl, 1-n-propyl-2-propenyl, 1-allyl-3-butenyl, 2-heptenyl, 1,5-dimethyl-4-hexenyl, 1-pentyl-2-propenyl, 1,7-dimethyl-6-octenyl and geranyl.

Examples of the C₂ -C₆ haloalkenyl group represented by R¹ are 2-chloroethenyl, 2,2-dichloroethenyl, 3-chloro-2-propenyl, 3-bromo-2-propenyl, 2-chloro-2-propenyl, 2-bromo-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 3,3-difluoro-2-propenyl, 2-(chloromethyl)-2-propenyl, 4-chloro-2-butenyl, 4-chloro-2-butenyl, 3-chloro-4,4,4-trifluoro-2-butenyl, 4-bromo-3-fluoro-4,4-difluoro-2-butenyl, 3,4,4,4-tetrafluoro-2-butenyl, 4,4-dichloro-3-butenyl, 4,4-dibromo-3-butenyl, 3-chloro-2-butenyl and 6,6-dichloro-5-hexenyl.

Examples of the C₂ -C₄ alkenyl group represented by R⁹ are vinyl, isopropenyl, 1-propenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, allyl, 2-methyl-2-propenyl and 2-butenyl.

Examples of the C₂ -C₄ haloalkenyl group represented by R⁹ are 2,2-dichloroethenyl, 2,2-dibromoethenyl, 3,3-dichloroallyl, 3,3-dibromoallyl, 2,3-dichloroallyl, 2,3-dibromoallyl, 2-chloro-2-propenyl, 3-chloro-2-propenyl, 2-bromo-2-propenyl and 3-chloro-2-butenyl.

Examples of the C₃ -C₉ alkynyl group represented by R¹ are 2-propynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 2-methyl-3-butynyl, 1-methyl-3-butynyl, 2-pentynyl, 4-pentynyl, 3-pentynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 5-hexynyl, 1-pentyl-2-propynyl and 3-nonynyl.

Examples of the C₃ -C₅ haloalkynyl group represented by R¹ are 3-chloro-2-propynyl, 3-bromo-2-propynyl, 4-chloro-2-butynyl, 3-chloro-1-methyl-2-propynyl, 3-bromo-1-methyl-2-propynyl, 4-chloro-3-butynyl, 4-bromo-3-butynyl, 4-chloro-2-methyl-3-butynyl, 4-bromo-2-methyl-3-butynyl, 1-methyl-4-chloro-3-butynyl, 1-methyl-4-bromo-3-butynyl, 5-chloro-4-pentynyl, 5-bromo-4-pentynyl, 1-ethyl-3-chloro-2-propynyl and 1-ethyl-3-bromo-2-propynyl.

Examples of the C₂ -C₄ alkynyl group represented by R⁹ are ethynyl, 1-propynyl, 2-propynyl and 1-methyl-2-propynyl.

Examples of the C₂ -C₄ haloalkynyl group represented by R⁹ are chloroethynyl, bromoethynyl, iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 3-iodo-2-propynyl, 1-methyl-3-chloro-2-propynyl, 1-methyl-3-bromo-2-propynyl and 1-methyl-3-iodo-2-propynyl.

Examples of the C₂ -C₄ alkynyloxy group represented by R⁹ are ethynyloxy, 1-propynyloxy, 2-propynyloxy and 1-methyl-2-propynyloxy.

Examples of the C₂ -C₄ haloalkynyloxy group represented by R⁹ are chloroethynyloxy, 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy, 1-methyl-3-chloro-2-propynyloxy and 1-methyl-3-bromo-2-propynyloxy.

Examples of the C₂ -C₇ alkoxyalkyl group represented by R¹ are methoxymethyl, 2-methoxyethyl, ethoxymethyl, isopropoxymethyl, n-propoxymethyl, 1-methoxyethyl, 2-ethoxyethyl, 1-ethoxyethyl, 3-methoxypropyl, 2-methoxypropyl, 1-methoxypropyl, 2-methoxy-1-methylethyl, n-propoxyethyl, 2-ethoxypropyl, 2-ethoxy-1-methylethyl, 2-methoxybutyl, 2-methoxy-1-ethylethyl, 3-ethoxypropyl, 3-methoxy-n-butyl, 3-methoxy-2-methylpropyl, 3-methoxy-1-methylpropyl, 2-isopropoxyethyl, 3-methoxybutyl, 3-methyl-3-methoxybutyl, 2-butoxyethyl and 2-butoxy-1-methylethyl.

Examples of the C₂ -C₄ alkoxyalkyl group represented by R⁹ are methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, 2-methoxyethyl, 1-methoxyethyl, 2-ethoxyethyl, 1-ethoxyethyl, 3-methoxypropyl, 2-methoxypropyl, 1-methoxypropyl and 2-methoxy-1-methylethyl.

Examples of the C₂ -C₇ alkylthioalkyl group represented by R¹ are methylthiomethyl, ethylthiomethyl, 2-methylthioethyl, 1-methylthioethyl, propylthiomethyl, isopropylthiomethyl, 2-ethylthioethyl, 1-ethylthioethyl, 3-(methylthio)propyl, 2-(methylthio)propyl, 1-(methylthio)propyl, 1-methyl-2-methylthioethyl, 2-isopropylthioethyl, 2-(propylthio)ethyl, 2-methylthio-1,2-dimethylethyl, 2-(methylthio)butyl, 1-ethyl-2-methylthioethyl, 2-(ethylthio)propyl, 2-ethylthio-1-methylethyl, 3-(ethylthio)propyl, 3-(methylthio)butyl, 2-methyl-3-(methylthio)propyl, 1-methyl-3-(methylthio)propyl, 2-tert-butylthioethyl, 2-isobutylthioethyl, 2-sec-butylthioethyl, 3-(tert-butylthio)propyl, 3-(isobutylthio)propyl and 3-(sec-butylthio)propyl.

Examples of the C₂ -C₄ alkylthioalkyl group represented by R⁹ are methylthiomethyl, ethylthiomethyl, propylthiomethyl, isopropylthiomethyl, 2-methylthioethyl, 1-methylthioethyl, 2-ethylthioethyl, 1-ethylthioethyl, 3-methylthiopropyl, 2-methylthiopropyl, 1-methylthiopropyl and 2-methylthio-1-methylethyl.

Examples of the C₃ -C₆ cycloalkyl group represented by R¹, which may be substituted with C₁ -C₄ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy, are cyclopropyl, cyclobutyl, 2-methoxycyclopentyl, 2-ethoxycyclopentyl, 2-propoxycyclopentyl, 2-isopropoxycyclohexyl, 2-butoxycyclopentyl, 2-isobutyloxycyclocpentyl, 2-sec-butyloxycyclopentyl, 2-tert-butyloxycyclopentyl, cyclopentyl, 3-methylcyclopentyl, 2-methylcyclopentyl, 3-methoxycyclohexyl, 3-ethoxycyclohexyl, 3-propoxycyclohexyl, 3-isopropoxycyclohexyl, 3-butoxycyclohexyl, 3-isobutyloxycyclohexyl, 3-sec-butyloxycyclohexyl, 3-tert-butyloxycyclohexyl, 4-methoxycyclohexyl, 4-ethoxycyclohexyl, 4-propoxycyclohexyl, 4-isopropoxycyclohexyl, 4-butoxycyclohexyl, 4-isobutyloxycyclohexyl, 4-sec-butyloxycyclohexyl and 4-tert-butyloxycyclohexyl.

Examples of the C₄ -C₉ cycloalkylalkyl group represented by R¹, which may be substituted with C₁ -C₄ alkyl, are cyclopropylmethyl, cyclobutylmethyl, 1-cyclopropylethyl, 2-methylcyclopropylmethyl, 2-(2-methylcyclopropyl)ethyl, cyclopentylmethyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclopentylpropyl and 3-cyclohexylpropyl.

Examples of the C₅ -C₆ cycloalkenyl group represented by R¹, which may be substituted with C₁ -C₄ alkyl, are 2-cyclohexenyl, 3,5,5-trimethyl-2-cyclohexenyl, 3-methyl-2-cyclohexenyl, 3-cyclohexenyl, 2-cyclopentenyl and 3-cyclopentenyl.

Examples of the C₆ -C₈ cycloalkenylalkyl group represented by R¹, which may be substituted with C₁ -C₄ alkyl, are (1-cyclopentenyl)methyl, (3-cyclohexenyl)methyl and 2-(3-cyclohexenyl)ethyl.

Examples of the C₃ -C₆ cycloalkyl group represented by R⁹ are cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Examples of the C₅ -C₆ cycloalkenyl group represented by R⁹ are 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl and 3-cyclohexenyl.

Examples of the C₃ -C₆ cycloalkyloxy group represented by R⁹ are cyclopropyloxy, cyclobutyloxy, cyclopentyloxy and cyclohexyloxy.

Examples of the C₅ -C₆ cycloalkenyloxy group represented by R⁹ are 1-cyclopentenyloxy, 2-cyclopentenyloxy, 3-cyclopentenyloxy, 1-cyclohexenyloxy, 2-cyclohexenyloxy and 3-cyclohexenyloxy.

Examples of the C₁ -C₃ alkoxy group present in R¹ or R⁹, or represented by R⁴ or R¹² are methoxy, ethoxy, n-propoxy and isopropoxy.

Examples of the (C₁ -C₃)alkoxy(C₁ -C₇)carbonylalkyl group represented by R¹ are 1-(ethoxycarbonyl)methyl, 1-(methoxycarbonyl)methyl, 1-(n-propoxycarbonyl)methyl, 2-(methoxycarbonyl)ethyl, 1-(isopropoxycarbonyl)methyl, 3-(methoxycarbonyl)propyl, 4-(methoxycarbonyl)butyl, 5-(methoxycarbonyl)pentyl, 6-(methoxycarbonyl)hexyl and 7-(methoxycarbonyl)heptyl.

Examples of the C₁ -C₈ alkoxy group represented by R⁹ are methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, (1-ethylpropyl)oxy, n-hexyloxy, octyloxy and n-heptyloxy.

Examples of the C₁ -C₃ haloalkoxy group present in R¹ or represented by R⁴ or R⁹ are trifluoromethoxy, difluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 1,2,2,3,3,3-hexafluoropropoxy, 3-fluoropropoxy, 3-chloropropoxy, 3-bromopropoxy, 2,2,3,3,3-pentafluoropropoxy, 3,3,3-trifluoropropoxy and 1,1,2,2,2-pentafluoroethoxy.

Examples of the C₁ -C₃ alkylthio group represented by R⁹ are methylthio, ethylthio, n-propylthio and isopropylthio.

Examples of the C₁ -C₃ haloalkylthio group represented by R⁹ are trifluoromethylthio, difluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, 2-bromo-1,1,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloroethylthio, 2-fluoroethylthio, 2-bromoethylthio, 3-fluoropropylthio, 3-chloropropylthio, (3-bromopropyl)thio, 2,2,3,3,3-pentafluoropropylthio and 3,3,3-trifluoropropylthio.

Examples of the C₃ -C₆ alkenyloxy group represented by R⁹ are allyloxy, 2-methylallyloxy, 2-butenyloxy, 3-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 2-pentenyloxy and 2-hexenyloxy.

Examples of the C₃ -C₆ haloalkenyloxy group represented by R⁹ are 3,3-dichloroallyloxy, 3,3-dibromoallyloxy, 2,3-dichloroallyloxy, 2,3-dibromoallyloxy, 2-chloro-2-propenyloxy, 3-chloro-2-propenyloxy, 2-bromo-2-propenyloxy and 3-chloro-2-butenyloxy.

Examples of the C₁ -C₃ hydroxyalkyl group represented by R⁹ are hydroxymethyl, 2-hydroxyethyl, 1-hydroxyethyl, 3-hydroxypropyl, 2-hydropropyl and 1-hydroxypropyl.

Examples of the C₂ -C₅ alkoxycarbonyl group represented by R⁹ are methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl and tert-butoxycarbonyl.

The following are preferred examples of the present compound:

dihalopropene compounds wherein R² and R³ are independently halogen or C₁ -C₃ alkyl, and r is 0;

dihalopropene compounds wherein R² and R³ are independently chlorine, bromine, methyl, ethyl or isopropyl, and r is 0;

dihalopropene compounds wherein R² and R³ are both chlorine, and r is 0;

dihalopropene compounds wherein R² is chlorine, R³ is methyl, and r is 0;

dihalopropene compounds wherein R² is ethyl, R³ is methyl, and r is 0;

dihalopropene compounds wherein R² is ethyl, R³ is methyl, and r is 0;

dihalopropene compounds wherein R² and R³ are both bromine, and r is 0;

dihalopropene compounds wherein R² and R³ are both ethyl, and r is 0;

dihalopropene compounds wherein R² and R³ are independently halogen or C₁ -C₃ alkyl, r is 1 or 2, and R¹⁴ is halogen or C₁ -C₃ alkyl;

dihalopropene compounds wherein R² and R³ are independently halogen or C₁ -C₃ alkyl, r is 1 or 2, and R¹⁴ is halogen;

dihalopropene compounds wherein Y and Z are both oxygen;

dihalopropene compounds wherein R¹ is Q₃ ;

dihalopropene compounds wherein R¹ is Q₃, p is 0, and R⁹ is halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio, cyano, nitro or 3,4-methylenedioxy;

dihalopropene compounds wherein R¹ is Q₃, p is, 0, R⁹ is phenyl which may be substituted with halogen, pentafluorosulfanyl, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; benzyl which may be substituted with halogen, pentafluorosulfanyl, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; phenoxy which may be substituted with halogen, pentafluorosulfanyl, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; or benzyloxy which may be substituted with halogen, pentafluorosulfanyl, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy;

dihalopropene compounds wherein R¹ is Q₃, p is 1 to 3, R¹⁰ and R¹¹ are both hydrogen, and R⁹ is halogen, trifluoromethyl, pentafluorosulfanyl or C₁ -C₃ haloalkoxy;

dihalopropene compounds wherein R¹ is Q₅ ;

dihalopropene compounds wherein R¹ is Q₅, p is 1 to 4, R¹⁰ and R¹¹ are both hydrogen, and R⁹ is halogen, trifluoromethyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, pentafluorosulfanyl or pentafluorosulfanyl;

dihalopropene compounds wherein R¹ is Q₅, p is 2 or 3, R¹⁰ and R¹¹ are both hydrogen, R⁹ is halogen, trifluoromethyl, isopropyloxy, C₁ -C₃ haloalkoxy, pentafluorosulfanyl or difluoromethylenedioxy, and A is oxygen;

dihalopropene compounds wherein R¹ is Q₅, p is 2 or 3, R¹⁰ and R¹¹ are both hydrogen, R⁹ is halogen, trifluoromethyl, isopropyloxy or C₁ -C₃ haloalkoxy, and A is oxygen; and

dihalopropene compounds wherein R¹ is C₁ -C₁₀ alkyl, C₁ -C₅ haloalkyl, C₂ -C₁₀ alkenyl, C₂ -C₆ haloalkenyl, C₃ -C₉ alkynyl, C₃ -C₅ haloalkynyl, C₂ -C₇ alkoxyalkyl, alkyl, (C₁ -C₃)alkoxy(C₁ -C₇)carbonylalkyl or C₂ -C₇ alkylthioalkyl; C₃ -C₆ cycloalkyl which may be substituted with C₁ -C₄ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; C₄ -C₉ cycloalkylalkyl which may be substituted with C₁ -C₄ alkyl; C₅ -C₆ cycloalkenyl which may be substituted with C₁ -C₄ alkyl; or C₆ -C₈ cycloalkenylalkyl which may be substituted with C₁ -C₄ alkyl.

The following are particularly preferred examples of the present compound wherein numbers in parentheses are the corresponding compound numbers used below:

(100) 3,5-Dichloro-4-(3-(4-trifluoromethoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene;

(166) 3,5-Dichloro-4-(3-(4-trifluoromethylphenoxy) propyl oxy)-1-(3,3-dichloro-2-propenyloxy)benzene;

(203) 3,5-Dichloro-4-(4-(4-isopropyloxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene;

(222) 3,5-Dichloro-4-(4-(4-chlorophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene; and

(284) 3-Ethyl-5-methyl-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.

The present compounds can be produced, for example, by the following production processes A-G.

(Production Process A)

In this process, a compound of the general formula: ##STR7## wherein R¹, R², R³, R ¹⁴, r, Y and Z are each as defined above, is reacted with a halide compound of the general formula:

    L--CH.sub.2 CH═CX.sub.2                                 VII!

wherein X is as defined above and L is halogen (e.g., chlorine, bromine, iodine), mesyloxy or tosyloxy.

The reaction is preferably effected in an inert solvent in the presence of a suitable base.

Examples of the solvent that can be used are ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C₁ -C₄) ether (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide, dimethylsulfoxide, hexamethylphophoric triamide, sulforane, acetonitrile, nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; and water. If necessary, a mixture of these solvents can be used.

Examples of the base which can be used are hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides (e.g., C₁ -C₄), such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; and organic bases such as triethylamine and pyridine. If necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system at a ratio of 0.01 to 1 mole per mole of the compound of the general formula VI!.

The reaction temperature is usually set within the range of -20° C. to 150° C. or the boiling point of a solvent used in the reaction, preferably -5° C. to 100° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the starting materials and bases to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out, if necessary, by an ordinary technique such as chromatography, distillation or recrystallization.

(Production Process B for the present compounds wherein Y is oxygen)

In this process, a compound of the general formula VI! is reacted with an alcohol compound of the general formula:

    HO--CH.sub.2 CH═CX.sub.2                                VIII!

wherein X is as defined above.

The reaction is preferably effected in an inert solvent, if necessary, in the presence of a suitable dehydrating agent.

Examples of the dehydrating agent which can be used are dicyclohexylcarbodiimide, and dialkyl (e.g., C₁ -C₄) azodicarboxylates (e.g. diethylazodicarboxylate, diisopropylazodicarboxylate)-trialkyl (e.g., C₁ -C₂₀) phosphine or triarylphosphine (e.g., triphenylphosphine, trioctylphosphine, tributylphosphine).

Examples of the solvent which can be used are hydrocarbons such as benzene, xylene and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene and dichlorobenzene.

The reaction temperature is usually set within the range of -20° C. to 200° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.

(Production Process C for the present compounds wherein Y is oxygen)

In this process, an aldehyde compound of the general formula: ##STR8## wherein R¹, R², R³, R¹⁴, r and Z are each as defined above, is reacted with carbon tetrachloride or carbon tetrabromide.

The reaction is preferably effected in an inert solvent in the presence of a suitable trialkylphosphine or triarylphosphine, and if necessary, in the presence of metal zinc.

Examples of the solvent which can be used are hydrocarbons such as benzene, xylene and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; and halogenated hydrocarbons (exclusive of carbon tetrabromide and carbon tetrachloride) such as dichloromethane, 1,2-dichloroethane and chlorobenzene.

The reaction temperature is usually set within the range of -30° C. to 150° C. or the boiling point of a solvent used in the reaction.

Examples of the trialkyl (e.g., C₁ -C₂₀) phosphine or triarylphosphine are triphenylphosphine and trioctylphosphine. The metal zinc which is used, if necessary, is preferably in dust form.

The molar ratio of the starting materials and reagents to be used in the reaction can be freely determined, but the ratio is preferably such that carbon tetrabromide or tetrachloride, trialkylphosphine or triarylphosphine, and zinc are 2 moles, 2 or 4 moles (2 moles when zinc is used), and 2 moles per mole of the aldehyde compound of the general formula IX!, or it is favorable to effect the reaction at a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.

(Production Process D for the present compounds wherein Y and Z are both oxygen)

In this process, a compound of the general formula: ##STR9## wherein R², R³, R¹⁴, r, Y and Z are each as defined above, is reacted with a compound of the general formula:

    R.sup.1 --L                                                 XI!

wherein R¹ and L are each as defined above.

The reaction is preferably effected in an inert solvent in the presence of a suitable base.

Examples of the solvent which can be used are ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C₁ -C₄) ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; and water. If necessary, a mixture of these solvents can be used.

Examples of the base which can be used are hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides (e.g., C₁ -C₄) such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; organic bases such as triethylamine and pyridine. If necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system at a ratio of 0.01 to 1 mole per mole of the compound of the general formula X!.

The reaction temperature is usually set within the range of -20° C. to 150° C. or the boiling point of a solvent used in the reaction, preferably -5° C. to 100° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.

(Production Process E for the present compounds wherein Y and Z are both oxygen)

In this process, a compound of the general formula X! is reacted with an alcohol compound of the general formula:

    R.sup.1 --OH                                                XII!

wherein R¹ is as defined above.

The reaction is preferably effected in an inert solvent, if necessary, in the presence of a suitable dehydrating agent.

Examples of the dehydrating agent which can be used are dicyclohexylcarbodiimide, and dialkyl (e.g., C₁ -C₄) azodicarboxylates (e.g., diethylazodicarboxylate, diisopropylazodicarboxylate)-trialkyl (e.g., C₁ -C₂₀) phosphine or triarylphosphine (e.g., triphenylphosphine, trioctylphosphine, tributylphosphine).

Examples of the solvent which can be used are hydrocarbons such as benzene, xylene and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene and dichlorobenzene.

The reaction temperature is usually set within the range of -20° C. to 200° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.

(Production Process F for the present compounds wherein Y and Z are both oxygen and R¹ is Q₅ (with the proviso that A is A²), Q₆ (with the proviso that A is A²), Q₇, Q₈ or Q₁₀ (with the proviso that A is A²) wherein A² is oxygen, sulfur or NR¹³ and R¹³ is as defined above!)

In this process, a compound of the general formula: ##STR10## wherein R², R³, R⁷, R¹⁰, R¹¹, R¹⁴, X, L, p and r are each as defined above, is reacted with compound Q₅₁, Q₆₁, Q₇₁, Q₈₁ or Q₁₀₁ of the general formula: ##STR11## wherein R⁴, R⁵, R⁶, R¹², R¹⁵, R¹⁶, Z¹, A² l , m, q and s are each as defined above.

The reaction is preferably effected in an inert solvent in the presence of a suitable base.

Examples of the solvent which can be used are ketones such as acetone, methyl ethyl ketone and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane and dialkyl (e.g., C₁ -C₄ ethers (e.g., diethyl ether, diisopropyl ether); N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; and water. If necessary, a mixture of these solvents can be used.

Examples of the base which can be used are hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal alkoxides (e.g., C₁ -C₄) such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; organic bases such as triethylamine and pyridine. If necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system at a ratio of 0.01 to 1 mole per mole of the compound of the general formula XIII!.

The reaction temperature is usually set within the range of -20° C. to 150° C. or the boiling point of a solvent used in the reaction, preferably -5° C. to 100° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the starting materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.

(Production Process G for the present compounds wherein Y and Z are both oxygen and R¹ is Q₅ (with the proviso that A is oxygen), Q₆ (with the proviso that A is oxygen), Q₇, Q₈ or Q₁₀ (with the proviso that A is oxygen))

In this process, a compound of the general formula: ##STR12## wherein R², R³, R⁷, R¹⁰, R¹¹, R¹⁴, X, p and r are each as defined above, is reacted with compound Q₅₂, Q₆₂, Q₇₁, Q₈₁ or Q₁₀₂ of the general formula: ##STR13## wherein R⁴, R⁵, R⁶, R12 R¹⁵, R¹⁶, Z¹ l, m, q and s are each as defined above.

The reaction is preferably effected in an inert solvent, if necessary, in the presence of a suitable dehydrating agent.

Examples of the dehydrating agent which can be used are dicyclohexylcarbodiimide, and dialkyl (e.g., C₁ -C₄) azodicarboxylates (e.g., diethylazodicarboxylate, diisopropylazodicarboxylate)-trialkyl (e.g., C₁ -C₂₀) phosphine or triarylphosphine (e.g., triphenylphosphine, trioctylphosphine, tributylphosphine).

Examples of the solvent which can be used are hydrocarbons such as benzene, xylene and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran and dioxane; and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene and dichlorobenzene.

The reaction temperature is usually set within the range of -20° C. to 200° C. or the boiling point of a solvent used in the reaction.

The molar ratio of the materials and dehydrating agents to be used in the reaction can be freely determined, but it is favorable to effect the reaction at an equimolar ratio or a ratio closer thereto.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as organic solvent extraction and concentration, and the desired compound of the present invention can be isolated. Further, purification can be carried out by an ordinary technique such as chromatography, distillation or recrystallization.

When the present compound has an asymmetry carbon atom, it is to be construed to include its optically active isomers ((+)-form and (-)-form) having biological activity and their mixtures at any ratio. When the present compound exhibits geometrical isomerism, it is to be construed to include its geometrical isomers (cis-form and transform) and their mixtures at any ratio.

The following are typical examples of the present compound (wherein R¹ is as shown in Tables 1 to 17), which are not to be construed to limit the scope of the present invention. ##STR14##

                  TABLE 1     ______________________________________     R.sup.1            R.sup.1     ______________________________________     CH.sub.3 --        CH.sub.3 CH.sub.2 CH(CH.sub.3)(CH.sub.2).sub.2 --     C.sub.2 H.sub.5 -- (CH.sub.3).sub.2 CHCH.sub.2 CH(CH.sub.3)--     CH.sub.3 CH.sub.2 CH.sub.2 --                        CH.sub.3 (CH.sub.2).sub.5 CH(CH.sub.3)--     (CH.sub.3).sub.2 CH--                        CH.sub.3 (CH.sub.2).sub.6 CH(CH.sub.3)--     CH.sub.3 (CH.sub.2).sub.2 CH.sub.2 --                        CF.sub.3 --     (CH.sub.3).sub.2 CHCH.sub.2 --                        CF.sub.2 H--     CH.sub.3 CH.sub.2 CH(CH.sub.3)--                        CF.sub.2 Br--     (CH.sub.3).sub.3 C--                        CF.sub.3 CH.sub.2 --     CH.sub.3 (CH.sub.2).sub.3 CH.sub.2 --                        CF.sub.3 CF.sub.2 --     (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 --                        FCH.sub.2 CH.sub.2 --     (CH.sub.3).sub.3 CCH.sub.2 --                        ClCH.sub.2 CH.sub.2 --     CH.sub.3 CH.sub.2 C(CH.sub.3).sub.2 --                        BrCH.sub.2 CH.sub.2 --     CH.sub.3 (CH.sub.2).sub.4 CH.sub.2 --                        ICH.sub.2 CH.sub.2 --     (CH.sub.3).sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2 --                        (Cl).sub.2 CHCH.sub.2 --     CH.sub.3 (CH.sub.2).sub.5 CH.sub.2 --                        BrCF.sub.2 CF.sub.2 --     CH.sub.3 (CH.sub.2).sub.6 CH.sub.2 --                        CF.sub.2 HCF.sub.2 --     CH.sub.3 (CH.sub.2).sub.7 CH.sub.2 --                        CFClHCF.sub.2 --     CH.sub.3 (CH.sub.2).sub.8 CH.sub.2 --                        CF.sub.2 BrCFH--     (C.sub.2 H.sub.5).sub.2 CH--                        ClCH.sub.2 CH.sub.2 CH.sub.2 --     (C.sub.2 H.sub.5).sub.2 CHCH.sub.2 --                        BrCH.sub.2 CH.sub.2 CH.sub.2 --     CH.sub.3 (CH.sub.2).sub.3 CH(CH.sub.3)--                        FCH.sub.2 CH.sub.2 CH.sub.2 --     CH.sub.3 (CH.sub.2).sub.2 CH(C.sub.2 H.sub.5)--                        ICH.sub.2 CH.sub.2 CH.sub.2 --     ______________________________________

                  TABLE 2     ______________________________________     CF.sub.3 CH.sub.2 CH.sub.2 --                      CH.sub.2 BrCH(CH.sub.2 Br)--     CF.sub.3 CF.sub.2 CH.sub.2 --                      CH.sub.2 BrCH.sub.2 CH(CH.sub.2 Br)--     CF.sub.3 CFHCF.sub.2 --                      CF.sub.3 CH(CF.sub.3)--     FCH.sub.2 (CH.sub.2).sub.3 --                      CH.sub.2 ═CH--     BrCH.sub.2 (CH.sub.2).sub.3 --                      CHCl═CH--     ClCH.sub.2 (CH.sub.2).sub.3 --                      CCl.sub.2 ═CH--     ICH.sub.2 (CH.sub.2).sub.3 --                      CH.sub.2 ═CHCH.sub.2 --     ClC(CH.sub.3).sub.2 CH.sub.2 --                      CH.sub.2 ═CHCH.sub.2 CH.sub.2 --     FCH.sub.2 (CH.sub.2).sub.4 --                      (CH.sub.3).sub.2 C═CH(CH.sub.2).sub.2 (CH.sub.3)C     BrCH.sub.2 (CH.sub.2).sub.4 --                      ═CHCH.sub.2 --     ClCH.sub.2 (CH.sub.2).sub.4 --                      (CH.sub.2 ═CH)(CH.sub.3 CH.sub.2 CH.sub.2)CH--     ICH.sub.2 (CH.sub.2).sub.4 --                      (CH.sub.2 ═CHCH.sub.2).sub.2 CH--     CH.sub.3 CHClCH.sub.2 --                      CH.sub.2 ═C(CH.sub.3)CH.sub.2 --     CH.sub.3 CH(CH.sub.2 Br)CH.sub.2 --                      (CH.sub.3).sub.2 C═CHCH.sub.2 --     CH.sub.2 ClC(CH.sub.3).sub.2 CH.sub.2 --                      CH.sub.2 ═C(CH.sub.3)CH.sub.2 CH.sub.2 --     CH.sub.2 BrC(CH.sub.3).sub.2 CH.sub.2 --                      (CH.sub.2 ═CH)(CH.sub.3 CH.sub.2)CH--     CH.sub.2 BrCHBrCH.sub.2 --                      ClCH═CHCH.sub.2 --     CCl.sub.3 CH.sub.2 --                      CH.sub.3 CH═CHCH.sub.2 --     CBr.sub.3 CH.sub.2 --                      BrCH═CHCH.sub.2 --     CF.sub.2 HCF.sub.2 CH.sub.2 --                      CH.sub.2 ═CClCH.sub.2 --     CF.sub.3 CFHCF.sub.2 CH.sub.2 --                      CH.sub.2 ═CBrCH.sub.2 --     CF.sub.2 H(CF.sub.2).sub.3 CH.sub.2 --                      CH.sub.2 ═C(CH.sub.2 Cl)CH.sub.2 --     CH.sub.2 ClCH(CH.sub.3)--                      ClCH.sub.2 CH═CHCH.sub.2 --     CH.sub.2 BrCH(CH.sub.3)--                      CH.sub.3 CH.sub.2 CH═CHCH.sub.2 CH.sub.2 --     CH.sub.2 FCH(CH.sub.2 F)--                      ClCH.sub.2 CH═CHCH.sub.2 --     CH.sub.2 ClCH(CH.sub.2 Cl)--                      (Cl.sub.2)C═CHCH.sub.2 --     ______________________________________

                                      TABLE 3     __________________________________________________________________________     (Br).sub.2 C═CHCH.sub.2 --                      CH.sub.3 CH═CH(CH.sub.2).sub.2 CH.sub.2 --     (F).sub.2 C═CHCH.sub.2 --                      CH.sub.2 ═CH(CH.sub.2).sub.3 CH.sub.2 --     (CF.sub.3)(Cl)C═CHCH.sub.2 --                      CH.sub.2 ═CHCH(CH.sub.3 CH.sub.2 CH.sub.2)--     (F)(CF.sub.2 Br)C═CHCH.sub.2 --                      (CH.sub.3).sub.2 C═CH(CH.sub.2).sub.2 CH(CH.sub.3)--                      3     (CF.sub.3)(F)C═CHCH.sub.2 CH.sub.2 --                      CH.sub.3 (CH.sub.2).sub.3 CH.sub.2 CH(CH═CH.sub.3)--                      0     (Cl).sub.2 C═CHCH.sub.2 CH.sub.2 --                      (CH.sub.3).sub.2 C═CH(CH.sub.2).sub.2 --CH(CH.sub.3)C                      H.sub.2 CH.sub.2 --     (Br).sub.2 C═CHCH.sub.2 CH.sub.2 --     CH.sub.2 ═C(CH(CH.sub.3).sub.2)CH.sub.2 --                      (CH.sub.3)(Cl)C═CHCH.sub.2 --     CH.sub.3 CH═C(C.sub.2 H.sub.5)CH.sub.2 --                      (Cl).sub.2 C═CH(CH.sub.2).sub.3 CH.sub.2 --     CH.sub.2 ═C(C.sub.2 H.sub.5)CH.sub.2 --                      CH.tbd.CCH(CH.sub.3)--     C.sub.2 H.sub.5 CH═C(CH.sub.3)CH.sub.2 --                      CH.sub.3 C.tbd.CCH.sub.2 --     C.sub.2 H.sub.5 CH═CHCH.sub.2 --                      HC.tbd.CCH.sub.2 --     CH.sub.3 CH═C(CH.sub.3)CH.sub.2 --                      HC.tbd.CCH.sub.2 CH.sub.2 --     CH.sub.3 (CH.sub.2).sub.3 CH═CHCH.sub.2 --                      CH.sub.3 CH.sub.2 CH.sub.2 C.tbd.CCH.sub.2 --     CH.sub.2 ═CHCH(CH.sub.3)--                      CH.sub.3 CH.sub.2 C.tbd.CCH.sub.2 CH.sub.2 --     CH.sub.3 CH═CHCH(CH.sub.3)--                      HC.tbd.CCH(CH.sub.3)CH.sub.2 --     CH.sub.3 CH═CHCH(C.sub.2 H.sub.5)--                      HC.tbd.CCH(CH.sub.3 (CH.sub.2).sub.4 --     CH.sub.2 ═CHCH.sub.2 CH.sub.2 CH(CH.sub.3)--                      HC.tbd.CCH.sub.2 CH(CH.sub.3)--     (CH.sub.3).sub.2 C═CHCH(CH.sub.3)--                      CH.sub.3 CH.sub.2 C.tbd.CCH.sub.2 --     CF.sub.3 CH═CHCH.sub.2 --                      HC.tbd.CCH.sub.2 CH.sub.2 CH.sub.2 --     CH.sub.2 ═CHCH(CH.sub.3)CH.sub.2 --                      CH.sub.3 C.tbd.CCH.sub.2 CH.sub.2 --     CH.sub.2 ═CHCH.sub.2 CH.sub.2 CH.sub.2 --                      HC.tbd.CCH(C.sub.2 H.sub.5)--     CH.sub.2 ═CHCH.sub.2 (CH.sub.3)CH--                      HC.tbd.CCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --     CH.sub.2 ═CHCH(C.sub.2 H.sub.5)--                      CH.sub.3 (CH.sub.2).sub.4 C.tbd.CCH.sub.2 CH.sub.2 --     CH.sub.3 (CH.sub.2).sub.2 CH═CHCH.sub.2                      ClCH.sub.2 C.tbd.CCH--     __________________________________________________________________________

                  TABLE 4     ______________________________________     ClC.tbd.CCH(CH.sub.3)--                        CH.sub.3 CH(OC.sub.2 H.sub.5)--     BrC.tbd.CCH(CH.sub.3)--                        CH.sub.2 (CH.sub.3 O)CH.sub.2 CH.sub.2 --     ClC.tbd.CCH.sub.2 --                        CH.sub.3 CH(CH.sub.3 O)CH.sub.2 --     BrC.tbd.CCH.sub.2 --                        CH.sub.3 CH.sub.2 CH(CH.sub.3 O)--     ClC.tbd.CCH.sub.2 CH.sub.2 --                        CH.sub.3 OCH.sub.2 CH(CH.sub.3)--     BrC.tbd.CCH.sub.2 CH.sub.2 --                        CH.sub.3 (CH.sub.2).sub.2 OCH.sub.2 CH.sub.2 --     ClC.tbd.CCH(CH.sub.3)CH.sub.2 --                        CH.sub.3 CH.sub.2 OCH(CH.sub.3)CH.sub.2 --     BrC.tbd.CCH(CH.sub.3)CH.sub.2 --                        CH.sub.3 CH.sub.2 OCH.sub.2 CH(CH.sub.3)--     ClC.tbd.CCH.sub.2 CH(CH.sub.3)--                        CH.sub.3 OCH(C.sub.2 H.sub.5)CH.sub.2 --     BrC.tbd.CCH.sub.2 CH(CH.sub.3)--                        CH.sub.3 OCH.sub.2 CH(C.sub.2 H.sub.5)--     ClC.tbd.CCH.sub.2 CH.sub.2 CH.sub.2 --                        C.sub.2 H.sub.5 OCH.sub.2 CH.sub.2 CH.sub.2 --     BrC.tbd.CCH.sub.2 CH.sub.2 CH.sub.2 --                        CH.sub.3 OCH(CH.sub.3)CH.sub.2 CH.sub.2 --     ClC.tbd.CCH(C.sub.2 H.sub.5)--                        CH.sub.3 OCH.sub.2 CH(CH.sub.3)CH.sub.2 --     BrC.tbd.CCH(C.sub.2 H.sub.5)--                        CH.sub.3 OCH.sub.2 CH.sub.2 CH(CH.sub.3)--     CH.sub.3 (CH.sub.2).sub.3 OCH.sub.2 CH(CH.sub.3)--                        CH.sub.3 SCH.sub.2 (CH.sub.2).sub.2 CH.sub.2 --     CH.sub.3 (CH.sub.2).sub.3 OCH.sub.2 CH.sub.2 --                        CH.sub.3 SCH.sub.2 --     (CH.sub.3).sub.2 CHOCH.sub.2 CH.sub.2 --                        CH.sub.3 CH.sub.2 SCH.sub.2 --     (CH.sub.3).sub.2 (CH.sub.3 O)CCH.sub.2 CH.sub.2 --                        CH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.2 --     CH.sub.3 (CH.sub.3 O)CHCH.sub.2 CH.sub.2 --                        (CH.sub.3).sub.2 CHSCH.sub.2 --     CH.sub.3 OCH.sub.2 CH.sub.2 --                        CH.sub.3 SCH.sub.2 CH.sub.2 --     CH.sub.3 CH.sub.2 OCH.sub.2 --                        CH.sub.3 SCH(CH.sub.3)--     CH.sub.3 OCH.sub.2 --                        CH.sub.3 CH.sub.2 SCH.sub.2 CH.sub.2 --     (CH.sub.3).sub.2 CHOCH.sub.2 --                        CH.sub.3 CH.sub.2 SCH(CH.sub.3)--     CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.2 --                        CH.sub.3 SCH.sub.2 CH.sub.2 CH.sub.2 --     CH.sub.3 CH(OCH.sub.3)--                        CH.sub.3 S(CH.sub.3)CHCH.sub.2 --     CH.sub.3 CH.sub.2 OCH.sub.2 CH.sub.2 --                        CH.sub.3 SCH(CH.sub.3 CH.sub.2)--     ______________________________________

                  TABLE 5     ______________________________________     CH.sub.3 SCH.sub.2 CH(CH.sub.3)--                         3-sec-butyloxycyclohexyl     (CH.sub.3).sub.2 CHSCH.sub.2 CH.sub.2 --                         3-tert-butyloxycyclohexyl     CH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.2 CH.sub.2 --                         4-methoxycyclohexyl     CH.sub.3 SCH(CH.sub.3)C(CH.sub.3)H--                         4-ethoxycyclohexyl     CH.sub.3 SCH(C.sub.2 H.sub.5)CH.sub.2 --                         4-propoxycyclohexyl     CH.sub.3 SCH.sub.2 CH(C.sub.2 H.sub.5)--                         4-isopropoxycyclohexyl     CH.sub.3 CH.sub.2 SCH(CH.sub.3)CH.sub.2 --                         4-butoxycyclohexyl     CH.sub.3 CH.sub.2 SCH.sub.2 CH(CH.sub.3)--                         4-isobutyloxycyclohexyl     CH.sub.3 CH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.2 --                         4-sec-butyloxycyclohexyl     CH.sub.3 SCH(CH.sub.3)CH.sub.2 CH.sub.2 --                         4-tert-butyloxycyclohexyl     CH.sub.3 SCH.sub.2 CH(CH.sub.3)CH.sub.2 --                         2-methoxycyclopentyl     CH.sub.3 SCH.sub.2 CH.sub.2 CH(CH.sub.3)--                         2-ethoxycyclopentyl     (CH.sub.3).sub.3 CSCH.sub.2 CH.sub.2 --                         2-propoxycyclopentyl     (CH.sub.3).sub.2 CHCH.sub.2 SCH.sub.2 CH.sub.2 --                         2-isopropoxycyclopentyl     CH.sub.3 CH.sub.2 CH(CH.sub.3)SCH.sub.2 CH.sub.2 --                         2-butoxycyclopentyl     (CH.sub.3).sub.3 CSCH.sub.2 CH.sub.2 CH.sub.2 --                         2-isobutyloxycyclopentyl     (CH.sub.3).sub.2 CHCH.sub.2 SCH.sub.2 CH.sub.2 CH.sub.2 --                         2-sec-butyloxycyclopentyl     CH.sub.3 CH.sub.2 CH(CH.sub.3)SCH.sub.2 CH.sub.2 CH.sub.2 --                         2-tert-butyloxycyclopentyl     3-methoxycyclohexyl cyclopropyl     3-ethoxycyclohexyl  cyclobutyl     3-propoxycyclohexyl cyclopentyl     3-isopropoxycyclohexyl     3-butoxycyclohexyl     3-isobutyloxycyclohexyl     ______________________________________

                  TABLE 6     ______________________________________     cyclohexyl        3-(difluorobromomethoxy)-     2,3-dimethylcyclohexyl                       cyclohexyl     2-ethylcyclohexyl 4-(difluorobromomethoxy)-     3,3,5,5-tetramethyl-                       cyclohexyl     cyclohexyl        3-(difluorobromomethoxy)-     3,4-dimethylcyclohexyl                       cyclopentyl     3,5-dimethylcyclohexy                       3-(2,2,2-trifluoromethoxy)-     4-ethylcyclohexyl cyclohexyl     2-methylcyclohexyl                       4-(2,2,2-trifluoroethoxy)-     3-methylcyclohexyl                       cyclohexyl     4-methylcyclohexyl                       3-(2,2,2-trifluoroethoxy)-     3-methylcyclopentyl                       cyclopentyl     2-methylcyclopentyl                       3-(1,1,2,2,2-pentafluoro-     3-(trifluoromethoxy)-                       ethoxy)cyclohexyl     cyclohexyl        4-(1,1,2,2,2-pentafluoro-     4-(trifluoromethoxy)-                       ethoxy)cyclohexyl     cyclohexyl        3-(1,1,2,2,2-pentafluoro-     3-(trifluoromethoxy)-                       ethoxy)cyclopentyl     cyclopentyl       3-(2-chloroethoxy)-     3-(difluoromethoxy)-                       cyclohexyl     cyclohexyl        3-(2-chloroethoxy)-     4-(difluoromethoxy)-                       cyclopentyl     cyclohexyl        4-(2-chloroethoxy)-     3-(difluoromethoxy)-                       cyclohexyl     cyclopentyl       3-(2-bromoethoxy)-                       cyclohexyl     ______________________________________

                  TABLE 7     ______________________________________     3-(2-bromoethoxy)- 3-(1,2,2,3,3,3-hexafluoro-     cyclopentyl        propoxy)cyclopentyl     4-(2-bromoethoxy)- 4-(1,2,2,3,3,3-hexafluoro-     cyclohexyl         propoxy)cyclohexyl     3-(2-chloro-1,1,2-trifluoro-                        2-cyclohexylethyl     ethoxy)cyclohexyl  cyclobutylmethyl     3-(2-chloro-1,1,2-trifluoro-                        cyclopropylmethyl     ethoxy)cyclopentyl 1-cyclopropylmethyl     4-(2-chloro-1,1,2-trifluoro-                        cyclohexylmethyl     ethoxy)cyclohexyl  cyclopentylmethyl     3-(2-bromo-1,1,2-trifluoro-                        2-methylcyclopropanemethyl     ethoxy)cyclohexyl  3-cyclopentylpropyl     3-(2-bromo-1,1,2-trifluoro-                        3-cyclohexylpropyl     ethoxy)cyclopentyl 2-(2-methylcyclopropyl)ethyl     4-(2-bromo-1,1,2-trifluoro-                        2-cyclohexenyl     ethoxy)cyclohexyl  3,5,5-trimethyl-2-     3-(1,1,2,2-tetrafluoro-                        cyclohexenyl     ethoxy)cyclohexyl  3-methyl-2-cyclohexenyl     3-(1,1,2,2-tetrafluoro-                        2-(3-cyclohexenyl)ethyl     ethoxy)cyclopentyl (3-cyclohexenyl)methyl     4-(1,1,2,2-tetrafluoro-                        (1-cyclopentenyl)methyl     ethoxy)cyclohexyl  2-cyclopentenyl     3-(1,2,2,3,3,3-hexafluoro-                        3-cyclopentenyl     propoxy)cyclohexyl 3-cyclohexenyl     CH.sub.3 OCOCH.sub.2                        CH.sub.3 CH.sub.2 OCOCH.sub.2 CH.sub.2 CH.sub.2     CH.sub.3 OCOCH.sub.2 CH.sub.2                        CH.sub.3 CH.sub.2 CH.sub.2 OCOCH.sub.2 CH.sub.2     CH.sub.3 OCOCH.sub.2 CH.sub.2 CH.sub.2                        (CH.sub.3).sub.2 CHOCOCH.sub.2 CH.sub.2     CH.sub.3 OCOCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                        CH.sub.3 CH.sub.2 OCOCH.sub.2 CH.sub.2 CH.sub.2     CH.sub.3 OCOCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                        CH.sub.3 CH.sub.2 CH.sub.2 OCOCH.sub.2 CH.sub.2                        CH.sub.2     CH.sub.3 OCOCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                        (CH.sub.3).sub.2 CHOCOCH.sub.2 CH.sub.2 CH.sub.2     CH.sub.3 OCOCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2     ______________________________________     CH.sub.2

                                      TABLE 8     __________________________________________________________________________      ##STR15##     (R.sup.4).sub.m            (R.sup.12).sub.a                    ##STR16##  p R.sup.7                                       R.sup.16                                          R.sup.11     __________________________________________________________________________     H      H      1           1 H     H  H     H      H      1           0 H     H  H     H      H      2           0 H     H  H     H      H      2           1 H     H  H     H      H      2           0 CH.sub.3                                       H  H     H      H      1           0 CH.sub.3                                       H  H     6-CH.sub.3            H      2           0 CH.sub.3                                       H  H     6-OCH.sub.3            H      2           0 CH.sub.2 CH.sub.3                                       H  H     H      2-OCH.sub.3                   1           0 H     H  H     H      4-F    1           0 H     H  H     H      2-OCH.sub.2 CH.sub.3                   1           0 H     H  H     H      4-OCH.sub.3                   1           0 H     H  H     H      3-OCH.sub.3                   2           0 H     H  H     H      2-CH.sub.3                   1           0 H     H  H     6-OCF.sub.3            H      2           0 CH.sub.2 CH.sub.2                                       H  H     6-OCH.sub.2 CH.sub.3            H      2           0 CH.sub.2 CH.sub.2                                       H  H     6-OCH(CH.sub.3).sub.2            H      2           0 CH.sub.2 CH.sub.3                                       H  H     4-OCF.sub.3            H      1           0 H     H  H     4-OCH.sub.2 CH.sub.3            H      1           0 H     H  H     4-OCH(CH.sub.3).sub.2            H      1           0 H     H  H     H      1-CHF.sub.2                   2           0 H     H  H     H      H      2           1 H     CH.sub.3                                          H     6-OCF.sub.3            H      2           1 H     CH.sub.3                                          H     6-OCH(CH.sub.3).sub.2            H      2           1 H     CH.sub.3                                          H     H      H      3           1 H     CH.sub.3                                          H     6-OCF.sub.3            H      3           1 H     CH.sub.3                                          H     6-OCH(CH.sub.3).sub.2            H      3           1 H     CH.sub.3                                          H     __________________________________________________________________________

                                      TABLE 9     __________________________________________________________________________      ##STR17##     (R.sup.4).sub.m              R.sup.7                 R.sup.1                      ##STR18##  p R.sup.10                                       R.sup.11     __________________________________________________________________________     H        H  H   1           0 H   H     H        H  1-CH.sub.3                     2           0 H   H     H        H  4-CH.sub.3                     1           0 H   H     H        H  H   2           0 H   H     6-OCH.sub.3              H  H   2           0 H   H     6-OCH.sub.3              H  H   3           0 H   H     6,7-(OCH.sub.3).sub.2              H  H   2           0 H   H     H        H  2-CH.sub.3                     1           0 H   H     6,7-(OCH.sub.3).sub.2              H  H   1           0 H   H     5,7-(CH.sub.3).sub.3              H  H   1           0 H   H     7-(OCH.sub.3)              H  H   1           0 H   H     5-OCH.sub.3              H  H   1           0 H   H     6-OCH.sub.3              H  H   1           0 H   H     5-OCH.sub.4              H  H   1           0 H   H     5-OCH.sub.2 CH.sub.3              H  H   1           0 H   H     5-OCH.sub.2 CH.sub.2 CH.sub.3              H  H   1           0 H   H     5-OCH(CH.sub.3).sub.2              H  H   1           0 H   H     5-OCF.sub.3              H  H   1           0 H   H     5-OCF.sub.2 H              H  H   1           0 H   H     5-OCF.sub.2 Br              H  H   1           0 H   H     5-OCH.sub.2 CF.sub.3              H  H   1           0 H   H     5-OCF.sub.2 CF.sub.3              H  H   1           0 H   H     5-OCH.sub.2 CH.sub.2 CF.sub.3              H  H   1           0 H   H     H        H  H   2           1 H   H     H        H  H   2           2 H   H     H        H  H   1           1 H   H     H        H  H   1           2 H   H     6-OCH.sub.3              H  H   2           1 H   H     6-OCH.sub.3              H  H   2           2 H   H     6-OCH.sub.2 CH.sub.3              H  H   2           1 H   H     6-OCH.sub.2 CH.sub.3              H  H   2           2 H   H     6-OCH(CH.sub.3).sub.2              H  H   2           1 H   H     6-OCH(CH.sub.3).sub.2              H  H   2           2 H   H     H        CH.sub.3                 H   2           1 H   H     H        H  H   2           1 H   H     H        H  H   2           1 H   H     H        H  H   1           1 CH.sub.3                                       H     H        H  H   2           1 CH.sub.3                                       H     __________________________________________________________________________

                                      TABLE 10     __________________________________________________________________________      ##STR19##     (R.sup.4).sub.m            R.sup.7                R.sup.8                     ##STR20##   p  R.sup.16                                       R.sup.11     __________________________________________________________________________     H      H   3-Br                    2            0  H  H     H      H   H   1            0  H  H     H      H   H   2            0  H  H     H      H   H   2            1  H  H     H      H   H   2            2  H  H     H      H   H   1            1  H  H     H      H   H   1            2  H  H     5-F    H   H   1            0  H  H     5-F    H   H   1            1  H  H     5-F    H   H   1            2  H  H     5-OCH.sub.3            H   H   2            0  H  H     5-OCH.sub.3            H   H   1            0  H  H     5-OCH.sub.3            H   H   1            1  H  H     5-OCH.sub.3            H   H   1            2  H  H     6-OCH.sub.3            H   H   1            0  H  H     6-OCH.sub.3            H   H   1            1  H  H     6-OCH.sub.3            H   H   1            2  H  H     5,6-(OCH.sub.3).sub.2            H   H   1            0  H  H     5,6-(OCH.sub.3).sub.2            H   H   1            1  H  H     5,6-(OCH.sub.3).sub.2            H   H   1            2  H  H     H      CH.sub.3                H   2            1  H  H     H      H   H   2            1  H  H     H      H   H   1            1  H  H     H      H   H   1            1  CH.sub.3                                       H     H      H   H   2            1  CH.sub.3                                       H     __________________________________________________________________________

                  TABLE 11     ______________________________________      ##STR21##     (R.sup.4)l R.sup.5   R.sup.6 R.sup.7                                       R.sup.10                                            R.sup.11                                                 p     ______________________________________     H          H         H       H    H    H    0     H          H         Cl      H    H    H    0     H          H         F       H    H    H    0     H          H         Br      H    H    H    0     H          H         CH.sub.3                                  H    H    H    0     H          Br        H       H    H    H    0     H          CH.sub.3  H       H    H    H    0     H          CH.sub.3  H       H    H    H    0     H          CH.sub.2 CH.sub.3                          H       H    H    H    0     H          CH.sub.2 CH.sub.2 CH.sub.3                          H       H    H    H    0     H          CH(CH.sub.3).sub.2                          H       H    H    H    0     4-Cl       H         H       CH.sub.3                                       H    H    0     H          H         H       CH.sub.3                                       H    H    0     4-C(CH.sub.3)                H         CH.sub.3                                  H    H    H    0     2,4,5-(OCH.sub.3).sub.3                H         CH.sub.3                                  H    H    H    0     2-OCH.sub.3                H         H       H    H    H    0     2-F        H         H       H    H    H    0     2-CF.sub.3 H         H       H    H    H    0     2-Cl       H         H       H    H    H    0     3-F        H         H       H    H    H    0     3-Cl       H         H       H    H    H    0     3-Br       H         H       H    H    H    0     3-CF.sub.3 H         H       H    H    H    0     3-OCH.sub.3                H         H       H    H    H    0     4-F        H         H       H    H    H    0     4-CF.sub.3 H         H       H    H    H    0     4-Cl       H         H       H    H    H    0     4-Br       H         H       H    H    H    0     4-OCH.sub.3                H         H       H    H    H    0     2,6-F.sub.2                H         H       H    H    H    0     2,4-F.sub.2                H         H       H    H    H    0     2,5-F.sub.2                H         H       H    H    H    0     3,4-F.sub.2                H         H       H    H    H    0     3,5-F.sub.2                H         H       H    H    H    0     2,6-Cl.sub.2                H         H       H    H    H    0     2,4-Cl.sub.2                H         H       H    H    H    0     3,4-Cl.sub.2                H         H       H    H    H    0     2-OCH.sub.3, 5-Br                H         H       H    H    H    0     2,3-(OCH.sub.3).sub.2                H         H       H    H    H    0     2,4-(OCH.sub.3).sub.2                H         H       H    H    H    0     2,5-(OCH.sub.3).sub.2                H         H       H    H    H    0     3,4-(OCH.sub.3).sub.2                H         H       H    H    H    0     3,5-(OCH).sub.2                H         H       H    H    H    0     3,4,5-(OCH.sub.3).sub.3                H         H       H    H    H    0     2,4,5-(OCH.sub.3).sub.3                H         H       H    H    H    0     2,3,4,5,6-F.sub.5                H         H       H    H    H    0     4-OCH.sub.2 CH.sub.3                H         H       H    H    H    0     3-OCH.sub.2 CH.sub.3                H         H       H    H    H    0     3-OCH.sub.2 CH.sub.2 CH.sub.3                H         H       H    H    H    0     3-(OCH(CH.sub.3).sub.2                H         H       H    H    H    0     4-OCH.sub.2 CH.sub.2 CH                H         H       H    H    H    0     4-OCH(CH.sub.3).sub.2                H         H       H    H    H    0     3-OCF.sub.3                H         H       H    H    H    0     4-OCF.sub.3                H         H       H    H    H    0     3-OCHF.sub.2                H         H       H    H    H    0     4-OCHF.sub.2                H         H       H    H    H    0     3-OCF.sub.2 Br                H         H       H    H    H    0     4-OCF.sub.2 Br                H         H       H    H    H    0     3-OCH.sub.2 CF.sub.3                H         H       H    H    H    0     4-OCH.sub.2 CF.sub.3                H         H       H    H    H    0     3-OCF.sub.2 CF.sub.2 H                H         H       H    H    H    0     4-OCF.sub.2 CF.sub.2 H                H         H       H    H    H    0     3-OCH.sub.2 CH.sub.2 CF.sub.3                H         H       H    H    H    0     4-OCH.sub.2 CH.sub.2 CF.sub.3                H         H       H    H    H    0     3-OCF.sub.2 CPHCF.sub.3                H         H       H    H    H    0     4-OCF.sub.2 CFHCF.sub.3                H         H       H    H    H    0     3-CH.sub.3 H         H       H    H    H    0     4-CH.sub.3 H         H       H    H    H    0     3-CH.sub.2 CH.sub.3                H         H       H    H    H    0     4-CH.sub.2 CH.sub.3                H         H       H    H    H    0     2,4-(CH.sub.3).sub.2                H         H       H    H    H    0     2-CF.sub.3 H         H       H    H    H    0     2-CH.sub.3 H         H       H    H    H    0     4-CH(CH.sub.3).sub.2                H         H       H    H    H    0     3-CH.sub.3 H         H       H    H    H    0     4-CF.sub.3 H         H       H    H    H    0     3-CF.sub.3 H         H       H    H    H    0     4-Cl       H         H       H    H    H    1     4-CF.sub.3 H         H       H    H    H    1     4-OCH(CH.sub.3).sub.2                H         H       H    H    H    1     4-OCF.sub.3                H         H       H    H    H    1     3-F        H         H       H    H    H    1     3-CF.sub.3 H         H       H    H    H    1     ______________________________________

                  TABLE 12     ______________________________________      ##STR22##      ##STR23##      ##STR24##      ##STR25##      ##STR26##      ##STR27##      ##STR28##      ##STR29##      ##STR30##      ##STR31##      ##STR32##      ##STR33##      ##STR34##      ##STR35##      ##STR36##      ##STR37##      ##STR38##      ##STR39##      ##STR40##      ##STR41##      ##STR42##      ##STR43##      ##STR44##      ##STR45##      ##STR46##      ##STR47##      ##STR48##      ##STR49##      ##STR50##      ##STR51##      ##STR52##      ##STR53##      ##STR54##      ##STR55##      ##STR56##      ##STR57##      ##STR58##      ##STR59##      ##STR60##      ##STR61##      ##STR62##      ##STR63##      ##STR64##      ##STR65##      ##STR66##      ##STR67##      ##STR68##      ##STR69##      ##STR70##      ##STR71##      ##STR72##      ##STR73##      ##STR74##      ##STR75##      ##STR76##      ##STR77##      ##STR78##      ##STR79##      ##STR80##      ##STR81##      ##STR82##      ##STR83##      ##STR84##      ##STR85##      ##STR86##      ##STR87##      ##STR88##      ##STR89##      ##STR90##      ##STR91##      ##STR92##      ##STR93##      ##STR94##      ##STR95##      ##STR96##      ##STR97##      ##STR98##      ##STR99##      ##STR100##      ##STR101##      ##STR102##      ##STR103##      ##STR104##      ##STR105##      ##STR106##      ##STR107##      ##STR108##      ##STR109##      ##STR110##      ##STR111##      ##STR112##      ##STR113##      ##STR114##      ##STR115##      ##STR116##      ##STR117##      ##STR118##      ##STR119##      ##STR120##      ##STR121##      ##STR122##      ##STR123##      ##STR124##      ##STR125##      ##STR126##      ##STR127##      ##STR128##      ##STR129##      ##STR130##     ______________________________________     ((R.sup.9)l in Table 12 is as defined below.)            (R.sup.9)l     ______________________________________            H            2-CH.sub.3            2-F            2-CF.sub.3            2-Cl            2-Br            2-I            2-OCH.sub.3            2-OCH.sub.2 CH.sub.3            2-C.sub.6 H.sub.5            2-NO.sub.2            2-C.sub.6 H.sub.4 (p-CF.sub.3)            2-CH.sub.2 C.sub.6 H.sub.5            2-OC.sub.6 H.sub.5            2-CN            3-CH.sub.3            3-F            3-CF.sub.3            3-Cl            3-Br            3-I            3-OCH.sub.3            3-OC.sub.6 H.sub.5            3-OCH.sub.2 C.sub.6 H.sub.5            3-OCF.sub.3            3-OCF.sub.2 CF.sub.2 H            3-NO.sub.2            3-OC.sub.6 H.sub.4 (p-CH.sub.3)            3-OC.sub.6 H.sub.4 (p-C(CH.sub.3)3)            3-OC.sub.6 H.sub.4 (m-CF.sub.3)            3-OC.sub.6 H.sub.4 (p-Cl)            3-OC.sub.6 H.sub.3 (3,4-Cl.sub.2)            3-OC.sub.6 H.sub.3 (3,5-Cl.sub.2)            3-OC.sub.6 H.sub.4 (p-OCH.sub.3)            3-CN            3-CH.sub.3            3-CH.sub.2 CH.sub.3            3-CH.sub.2 CH.sub.2 CH.sub.3            3-CH(CH.sub.3).sub.2            3-C(CH.sub.3).sub.3            3-OCF.sub.2 Br            3-OCF.sub.2 H            3-OCF.sub.2 CFHCF.sub.3            3-OCH.sub.2 CF.sub.3            3-OCH.sub.2 CH.sub.3            3-OCH.sub.2 CH.sub.2 CH.sub.3            3-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            3-OCH(CH.sub.3).sub.2            3-OCH(CH.sub.3)CH.sub.2 CH.sub.3            3-OCH.sub.2 CH(CH.sub.3)CH.sub.3            3-OC(CH.sub.3).sub.3            3-OCH.sub.2 CHCH.sub.2            3-OCH.sub.2 CHC(Cl).sub.2            3-OCH.sub.2 CHC(Br).sub.2            3-OCH.sub.2 CHCH(Cl)            3-OCH.sub.2 C(Cl)CH(Cl)            3-OCH.sub.2 CHC(CH.sub.3).sub.2            3-OCH.sub.2 CHCH(CH.sub.3)            3-OCH.sub.2 C(CH.sub.3)CH.sub.2            3-OCH.sub.2 CBrCH(Br)            3-CH.sub.2 OH            3-CH.sub.2 OCH.sub.3            3-CH.sub.2 OCH.sub.2 CH.sub.3            3-CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3            3-CH.sub.2 OCH.sub.2 (CH.sub.3).sub.2            3-OCH.sub.2 CCH            3-OCH.sub.2 CC-Cl            3-OCH.sub.2 CC-Br            3-OCH.sub.2 CC-CH.sub.3            3-OCH(CH.sub.3)CCH            3-cyclopentyl            3-cyclohexyl            3-(3-cyclopentenyl)            3-(4-cyclopentenyl)             ##STR131##             ##STR132##             ##STR133##             ##STR134##             ##STR135##            3-cyclopropyloxy            3-cyclobutyloxy            3-cyclopentyloxy            3-cyclohexyloxy            3-(3-cyclohexenyl)            3-(4-cyclohexenyl)            3-(5-cyclohexenyl)            3-(3-cyclopentenyloxy)            3-(4-cyclopentenyloxy)            3-(3-cyclohexenyloxy)            3-(4-cyclohexenyloxy)            3-(5-cyclohexenyloxy)            3-CH.sub.2 C.sub.6 H.sub.5            3-OCH.sub.2 CHC(Cl)(CH.sub.3)            3-OCH.sub.2 CHC(CH.sub.3)(CF.sub.3)            3-OC.sub.6 H.sub.4 (o-Cl)            3-OC.sub.6 H.sub.4 (o-F)            3-OC.sub.6 H.sub.4 (o-CH.sub.3)            3-OC.sub.6 H.sub.4 (m-Cl)            3-OC.sub.6 H.sub.4 (m-F)            3-OC.sub.6 H.sub.4 (m-CH.sub.3)            3-OCH.sub.2 C.sub.6 H.sub.4 (o-Cl)            3-OCH.sub.2 C.sub.6 H.sub.4 (o-F)            3-OCH.sub.2 C.sub.6 H.sub.4 (o-Br)            3-OCH.sub.2 C.sub.6 H.sub.4 (o-CH.sub.3)            3-OCH.sub.2 C.sub.6 H.sub.4 (o-CF.sub.3)            3-OCH.sub.2 C.sub.6 H.sub.4 (m-Cl)            3-OCH.sub.2 C.sub.6 H.sub.4 (m-F)            3-OCH.sub.2 C.sub.6 H.sub.4 (m-Br)            3-OCH.sub.2 C.sub.6 H.sub.4 (m-CH.sub.3)            3-OCH.sub.2 C.sub.6 H.sub.4 (m-CF.sub.3)            3-OCH.sub.2 C.sub.6 H.sub.4 (p-Cl)            3-OCH.sub.2 C.sub.6 H.sub.4 (p-Br)            3-OCH.sub.2 C.sub.6 H.sub.4 (p-F)            3-OCH.sub.2 C.sub.6 H.sub.4 (p-CH.sub.3)            3-OCH.sub.2 C.sub.6 H.sub.4 (p-CF.sub.3)            3-SCF.sub.2 CF.sub.2 H            3-SCH.sub.3            3-SCH.sub.2 CH.sub.3            3-OCH.sub.2 C(Cl)CH.sub.2            4-CH.sub.3            4-CH.sub.2 CH.sub.3            4-CH(CH.sub.3).sub.2            4-C(CH.sub.3).sub.3            4-CH.sub.2 (CH.sub.2).sub.2 CH.sub.3            4-F            4-CF.sub.3            4-Cl            4-Br            4-OCH.sub.3            4-OCH.sub.2 CH.sub.3            4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            4-OCF.sub.3            4-C.sub.6 H.sub.5            4-OCH.sub.2 C.sub.6 H.sub.5            4-OCH.sub.2 CH.sub.2 CH.sub.3            4-OCF.sub.3            4-SCH.sub.3            4-NO.sub.2            4-OC.sub.6 H.sub.5            4-CH.sub.2 (CH.sub.2).sub.3 CH.sub.3            4-CH.sub.2 (CH.sub.2).sub.4 CH.sub.3            4-CH.sub.2 (CH.sub.2).sub.5 CH.sub.3            4-CH.sub.2 (CH.sub.2).sub.6 CH.sub.3            4-CHCH.sub.2            4-I            4-OCH.sub.2 (CH.sub.2).sub.3 CH.sub.3            4-OCH.sub.2 (CH.sub.2).sub.4 CH.sub.3            4-OCH.sub.2 (CH.sub.2).sub.5 CH.sub.3            4-OCH(CH.sub.3).sub.2            4-(2-cyclohexenyl)            4-SCH.sub.2 CH.sub.3            4-C.sub.6 H.sub.4 (p-CH.sub.2 CH.sub.3)            4-CN            4-OCF.sub.2 Br            4-OCF.sub.2 H            4-OCF.sub.2 CFHCF.sub.3            4-OCH.sub.2 CF.sub.3            4-OCF.sub.2 CF.sub.2 H            4-SCF.sub.2 CF.sub.2 H            4-SCH(CH.sub.3).sub.2            4-OCH.sub.2 CHCH.sub.2            4-OCH.sub.2 CHC(Cl).sub.2            4-OCH.sub.2 CHC(Br).sub.2            4-OCH.sub.2 CHCH(Cl)            4-OCH.sub.2 C(Cl)CH(Cl)            4-OCH.sub.2 CHC(CH.sub.3).sub.2            4-OCH.sub.2 CHCH(CH.sub.3)            4-OCH.sub.2 C(CH.sub.3)CH.sub.2            4-OCH.sub.2 C(Cl)CH.sub.2            4-OCH.sub.2 C(Br)CH.sub.2 (Br)            4-CH.sub.2 OH            4-CH.sub.2 OCH.sub.3            4-CH.sub.2 OCH.sub.2 CH.sub.3            4-CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3            4-CH.sub.2 OCH(CH.sub.3).sub.2            4-OCH.sub.2 CCH            4-OCH.sub.2 CC-Cl            4-OCH.sub.2 CC-Br            4-OCH.sub.2 CC-CH.sub.3            4-OCH(CH.sub.3)CCH            4-cyclopentyl            4-cyclohexyl            4-(3-cyclopentenyl)            4-(4-cyclopentenyl)             ##STR136##             ##STR137##             ##STR138##             ##STR139##             ##STR140##            4-cyclopropyloxy            4-cyclobutyloxy            4-cyclopentyloxy            4-cyclohexyloxy            4-(3-cyclohexenyl)            4-(4-cyclohexenyl)            4-(5-cyclohexenyl)            4-(3-cyclopentenyloxy)            4-(4-cyclopentenyloxy)            4-(3-cyclohexenyloxy)            4-(4-cyclohexenyloxy)            4-(5-cyclohexenyloxy)            4-CH.sub.2 C.sub.6 H.sub.5            4-OCH.sub.2 CHC(Cl)CH.sub.3            4-OCH.sub.2 CHC(CH.sub.3)CF.sub.3            4-OC.sub.6 H.sub.4 (o-Cl)            4-OC.sub.6 H.sub.4 (o-F)            4-OC.sub.6 H.sub.4 (o-CH.sub.3)            4-OC.sub.6 H.sub.4 (m-Cl)            4-OC.sub.6 H.sub.4 (m-F)            4-OC.sub.6 H.sub.4 (m-CH.sub.3)            4-OCH.sub.2 C.sub.6 H.sub.4 (o-Cl)            4-OCH.sub.2 C.sub.6 H.sub.4 (o-F)            4-OCH.sub.2 C.sub.6 H.sub.4 (o-Br)            4-OCH.sub.2 C.sub.6 H.sub.4 (o-CH.sub.3)            4-OCH.sub.2 C.sub.6 H.sub.4 (o-CF.sub.3)            4-OCH.sub.2 C.sub.6 H.sub.4 (m-Cl)            4-OCH.sub.2 C.sub.6 H.sub.4 (m-F)            4-OCH.sub.2 C.sub.6 H.sub.4 (m-Br)            4-OCH.sub.2 C.sub.6 H.sub.4 (m-CH.sub.3)            4-OCH.sub.2 C.sub.6 H.sub.4 (m-CF.sub.3)            4-OCH.sub.2 C.sub.6 H.sub.4 (p-Cl)            4-OCH.sub.2 C.sub.6 H.sub.4 (p-Br)            4-OCH.sub.2 C.sub.6 H.sub.4 (p-F)            4-OCH.sub.2 C.sub.6 H.sub.4 (p-CH.sub.3)            4-OCH.sub.2 C.sub.6 H.sub.4 (p-CF.sub.3)            4-SCF.sub.2 CF.sub.2 H            4-OCH.sub.2 C(Cl)CH.sub.2            2,6-F.sub.2            2,3-F.sub.2            2-F, 6-Cl            2,6-Cl.sub.2            2,3-(OCH.sub.3).sub.2            2,4-(CH.sub.3).sub.2            3,4-(CH.sub.3).sub.2            2,5-(CH.sub.3).sub.2            3,4-F.sub.2            2,4-F.sub.2            2,5-F.sub.2            2,4-Cl.sub.2            3,4-Cl.sub.2            2,5-Cl.sub.2            2,4-(OCH.sub.3).sub.2            2,5-(OCH.sub.3).sub.2            2-OCH.sub.3, 5-Br            3,4-OCH.sub.2 O            3,5-(CH.sub.3).sub.2            3,5-(CF.sub.3).sub.2            3,5-F.sub.2            3,5-Cl.sub.2            3,5-(OCH.sub.3).sub.2            2-CH.sub.3, 4-C.sub.6 H.sub.5            2-NO.sub.2, 4-Cl            2-NO.sub.2, 5-CH.sub.3            3-CH.sub.3, 4-NO.sub.2            3-NO.sub.2, 4-CH.sub.3            2-NO.sub.2, 4-Cl            3-NO.sub.2, 4-Cl            2-Cl, 5-NO.sub.2            2-NO.sub.2, 5-Cl            3-OCH.sub.3, 4-NO.sub.2            2-CH.sub.3, 3-F            2-F, 3-CF.sub.3            2,3-Cl.sub.2            2,6-(OCH.sub.3).sub.2            2-Cl, 6-NO.sub.2            2-NO.sub.2, 3-OCH.sub.3            2,6-(NO.sub.2).sub.2            2-Cl, 5-CF.sub.3            3-Cl, 4-F            2-Cl, 4-F            3-Br, 4-F            2-OCH.sub.3, 5-Br            3,4-OCH.sub.2 CH.sub.2 O            3-NO.sub.2, 5-Cl            2,4-(NO.sub.2).sub.2            3,5-(OCH.sub.2 C.sub.6 H.sub.5).sub.2            3,4-(OCH.sub.2 C.sub.6 H.sub.5).sub.2            2-F, 6-CF.sub.3            2-F, 3-CF.sub.3            2,6-(CF.sub.3).sub.2            2-NO.sub.2, 6-CH.sub.3            2-NO.sub.2, 3-CH.sub.3            2-CH.sub.3, 3-NO.sub.2            2-NO.sub.2, 3-Cl            2-Cl, 3-NO.sub.2            2-Br, 3-NO.sub.2            2-NO.sub.2, 3-OCH.sub.3            2-CH.sub.3, 5-F            3-F, 4-CH.sub.3            3-Br, 4-CH.sub.3            2,4-(CF.sub.3).sub.2            3-I, 4-CH.sub.3            2-Cl, 5-CF.sub.3            2,5-(CF.sub.3).sub.2            2-F, 4-CF.sub.3            2-Cl, 4-F            3-OCH.sub.3, 4-CH.sub.3            2-OCH.sub.3, 4-Cl            2-OCH.sub.3, 5-Cl            2-Br, 5-OCH.sub.3            3,4-(OCH.sub.2 CH.sub.3).sub.2            2-Cl, 5-SCH.sub.3            2-OCH.sub.3, 4-SCH.sub.3            3-CH.sub.3, 4-NO.sub.2            2-CH.sub.3, 5-NO.sub.2            2-NO.sub.2, 4-CF.sub.3            2-F, 5-NO.sub.2            2-Cl, 4-NO.sub.2            3-NO.sub.2, 4-F            2-Br, 5-NO.sub.2            3-NO.sub.2, 4-OCH.sub.3            3,5-(C(CH.sub.3).sub.3).sub.2            2,3(CH.sub.3).sub.2, 4-OCH.sub.3            3-CH.sub.3, 2,4-(OCH.sub.3).sub.2            2,3,4-(OCH.sub.3).sub.3            3,4,5-(OCH.sub.3).sub.3            2,3,4,5,6-F.sub.5            2,4,6-(CH.sub.3).sub.3            2,3,6-Cl.sub.3            3,4-(OCH.sub.3).sub.2, 5-Br            2,4,6-(OCH.sub.3).sub.3            2,4-(OCH.sub.3).sub.2, 5-Br            2-Br, 4,5-(OCH.sub.3).sub.2            2,4,5-(OCH.sub.3).sub.3            2-NO.sub.2, 3,4-(OCH.sub.3).sub.2            2-NO.sub.2, 3,4-OCH.sub.2 O            2,5-Cl.sub.2, 4-CHF.sub.2            2,3,4-F.sub.3            2,3,6-Cl.sub.3            2,3,5,6-F.sub.4            2,3,6-F.sub.3            2,4,6-F.sub.3            3,4,5-F.sub.3            2,4,6-Cl.sub.3            2,3,5-Cl.sub.3            2,3,5-I.sub.3            2,4,5-F.sub.3            2,4-Cl.sub.2, 5-F            2,3,4,5-F.sub.4            2,3,5,6-F.sub.4, 4-CH.sub.3            2,3,5,6-F.sub.4, 4-Br            3-Cl, 4-OCH.sub.3            3-Cl, 4-OCH.sub.2 CH.sub.3            3-Cl, 4-OCH.sub.2 CH.sub.2 CH.sub.3            3-Cl, 4-OCH(CH.sub.3).sub.2            3-Cl, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            3-Cl, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3            3-Cl, 4-OCH.sub.2 CH(CH.sub.3).sub.2            3-Cl, 4-OC(CH.sub.3).sub.3            3-Cl, 4-OCF.sub.3            3-Cl, 4-OCF.sub.2 Br            3-Cl, 4-OCF.sub.2 H            3-Cl, 4-OCF.sub.2 CF.sub.2 H            3-Cl, 4-OCF.sub.2 CFHCF.sub.3            3-Cl, 4-OCH.sub.2 CF.sub.3            3-Cl, 4-OC.sub.6 H.sub.5            3-Cl, 4-OCH.sub.2 C.sub.6 H.sub.5            3-Cl, 4-cyclopentyloxy            3-Cl, 4-cyclohexyloxy            3-Br, 4-OCH.sub.3            3-Br, 4-OCH.sub.2 CH.sub.3            3-Br, 4-OCH.sub.2 CH.sub.2 CH.sub.3            3-Br, 4-OCH(CH.sub.3).sub.2            3-Br, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            3-Br, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3            3-Br, 4-OCH.sub.2 CH(CH.sub.3).sub.2            3-Br, 4-OC(CH.sub.3).sub.3            3-Br, 4-OCF.sub.3            3-Br, 4-OCF.sub.2 Br            3-Br, 4-OCF.sub.2 H            3-Br, 4-OCF.sub.2 CF.sub.2 H            3-Br, 4-OCF.sub.2 CFHCF.sub.3            3-Br, 4-OCH.sub.2 CF.sub.3            3-Br, 4-OC.sub.6 H.sub.5            3-Br, 4-OCH.sub.2 C.sub.6 H.sub.5            3-Br, 4-cyclopentyloxy            3-Br, 4-cyclohexyloxy            3-F, 4-OCH.sub.3            3-F, 4-OCH.sub.2 CH.sub.3            3-F, 4-OCH.sub.2 CH.sub.2 CH.sub.3            3-F, 4-OCH(CH.sub.3).sub.2            3-F, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            3-F, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3            3-F, 4-OCH.sub.2 CH(CH.sub.3).sub.2            3-F, 4-OC(CH.sub.3)3            3-F, 4-OCF.sub.3            3-F, 4-OCF.sub.2 Br            3-F, 4-OCF.sub.2 H            3-F, 4-OCF.sub.2 CF.sub.2 H            3-F, 4-OCF.sub.2 CFHCF.sub.3            3-F, 4-OCH.sub.2 CF.sub.3            3-F, 4-OC.sub.6 H.sub.5            3-F, 4-OCH.sub.2 C.sub.6 H.sub.5            3-F, 4-cyclopentyloxy            3-F, 4-cyclohexyloxy            3-CH.sub.3, 4-OCH.sub.3            3-CH.sub.3, 4-OCH.sub.2 CH.sub.3            3-CH.sub.3, 4-OCH.sub.2 CH.sub.2 CH.sub.3            3-CH.sub.3, 4-OCH(CH.sub.3).sub.2            3-CH.sub.3, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            3-CH.sub.3, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3            3-CH.sub.3, 4-OCH.sub.2 CH(CH.sub.3).sub.2            3-CH.sub.3, 4-OC(CH.sub.3).sub.3            3-CH.sub.3, 4-OCF.sub.3            3-CH.sub.3, 4-OCF.sub.2 Br            3-CH.sub.3, 4-OCF.sub.2 H            3-CH.sub.3, 4-OCF.sub.2 CF.sub.2 H            3-CH.sub.3, 4-OCF.sub.2 CFHCF.sub.3            3-CH.sub.3, 4-OCH.sub.2 CF.sub.3            3-CH.sub.3, 4-OC.sub.6 H.sub.5            3-CH.sub.3, 4-OCH.sub.2 C.sub.6 H.sub.5            3-CH.sub.3, 4-cyclopentyloxy            3-CH.sub.3, 4-cyclohexyloxy            3-OCH.sub.3, 4-OCH.sub.3            3-OCH.sub.3, 4-OCH.sub.2 CH.sub.3            3-OCH.sub.3, 4-OCH.sub.2 CH.sub.2 CH.sub.3            3-OCH.sub.3, 4-OCH(CH.sub.3).sub.2            3-OCH.sub.3, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            3-OCH.sub.3, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3            3-OCH.sub.3, 4-OCH.sub.2 CH(CH.sub.3).sub.2            3-OCH.sub.3, 4-OC(CH.sub.3).sub.3            3-OCH.sub.3, 4-OCF.sub.3            3-OCH.sub.3, 4-OCF.sub.2 Br            3-OCH.sub.3, 4-OCF.sub.2 H            3-OCH.sub.3, 4-OCF.sub.2 CF.sub.2 H            3-OCH.sub.3, 4-OCF.sub.2 CFHCF.sub.3            3-OCH.sub.3, 4-OCH.sub.2 CF.sub.3            3-OCH.sub.3, 4-OC.sub.6 H.sub.5            3-OCH.sub.3, 4-OCH.sub.2 C.sub.6 H.sub.5            3-OCH.sub.3, 4-cyclopentyloxy            3-OCH.sub.3, 4-cyclohexyloxy            3-OCH.sub.2 CH.sub.3, 4-OCH.sub.3            3-OCH.sub.2 CH.sub.3, 4-OCH.sub.2 CH.sub.3            3-OCH.sub.2 CH.sub.3, 4-OCH.sub.2 CH.sub.2 CH.sub.3            3-OCH.sub.2 CH.sub.3, 4-OCH(CH.sub.3).sub.2            3-OCH.sub.2 CH.sub.3, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            3-OCH.sub.2 CH.sub.3, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3            3-OCH.sub.2 CH.sub.3, 4-OCH.sub.2 CH(CH.sub.3).sub.2            3-OCH.sub.2 CH.sub.3, 4-OC(CH.sub.3).sub.3            3-OCH.sub.2 CH.sub.3, 4-OCF.sub.3            3-OCH.sub.2 CH.sub.3, 4-OCF.sub.2 Br            3-OCH.sub.2 CH.sub.3, 4-OCF.sub.2 H            3-OCH.sub.2 CH.sub.3, 4-OCF.sub.2 CF.sub.2 H            3-OCH.sub.2 CH.sub.3, 4-OCF.sub.2 CFHCF.sub.3            3-OCH.sub.2 CH.sub.3, 4-OCH.sub.2 CF.sub.3            3-OCH.sub.2 CH.sub.3, 4-OC.sub.6 H.sub.5            3-OCH.sub.2 CH.sub.3, 4-OCH.sub.2 C.sub.6 H.sub.5            3-OCH.sub.2 CH.sub.3, 4-cyclopentyloxy            3-OCH.sub.2 CH.sub.3, 4-cyclohexyloxy            4-Cl, 3-OCH.sub.3            4-Cl, 3-OCH.sub.2 CH.sub.3            4-Cl, 3-OCH.sub.2 CH.sub.2 CH.sub.3            4-Cl, 3-OCH(CH.sub.3).sub.2            4-Cl, 3-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            4-Cl, 3-OCH(CH.sub.3)CH.sub.2 CH.sub.3            4-Cl, 3-OCH.sub.2 CH(CH.sub.3).sub.2            4-Cl, 3-OC(CH.sub.3).sub.3            4-Cl, 3-OCF.sub.3            4-Cl, 3-OCF.sub.2 Br            4-Cl, 3-OCF.sub.2 H            4-Cl, 3-OCF.sub.2 CF.sub.2 H            4-Cl, 3-OCF.sub.2 CFHCF.sub.3            4-Cl, 3-OCH.sub.2 CF.sub.3            4-Cl, 3-OC.sub.6 H.sub.5            4-Cl, 3-OCH.sub.2 C.sub.6 H.sub.5            4-Cl, 3-cyclopentyloxy            4-Cl, 3-cyclohexyloxy            4-Br, 3-OCH.sub.3            4-Br, 3-OCH.sub.2 CH.sub.3            4-Br, 3-OCH.sub.2 CH.sub.2 CH.sub.3            4-Br, 3-OCH(CH.sub.3).sub.2            4-Br, 3-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            4-Br, 3-OCH(CH.sub.3)CH.sub.2 CH.sub.3            4-Br, 3-OCH.sub.2 CH(CH.sub.3).sub.2            4-Br, 3-OC(CH.sub.3).sub.3            4-Br, 3-OCF.sub.3            4-Br, 3-OCF.sub.2 Br            4-Br, 3-OCF.sub.2 H            4-Br, 3-OCF.sub.2 CF.sub.2 H            4-Br, 3-OCF.sub.2 CFHCF.sub.3            4-Br, 3-OCH.sub.2 CF.sub.3            4-Br, 3-OC.sub.6 H.sub.5            4-Br, 3-OCH.sub.2 C.sub.6 H.sub.5            4-Br, 3-cyclopentyloxy            4-Br, 3-cyclohexyloxy            4-F, 3-OCH.sub.3            4-F, 3-OCH.sub.2 CH.sub.3            4-F, 3-OCH.sub.2 CH.sub.2 CH.sub.3            4-F, 3-OCH(CH.sub.3).sub.2            4-F, 3-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            4-F, 3-OCH(CH.sub.3)CH.sub.2 CH.sub.3            4-F, 3-OCH.sub.2 CH(CH.sub.3).sub.2            4-F, 3-OC(CH.sub.3).sub.3            4-F, 3-OCF.sub.3            4-F, 3-OCF.sub.2 Br            4-F, 3-OCF.sub.2 H            4-F, 3-OCF.sub.2 CF.sub.2 H            4-F, 3-OCF.sub.2 CFHCF.sub.3            4-F, 3-OCH.sub.2 CF.sub.3            4-F, 3-OC.sub.6 H.sub.5            4-F, 3-OCH.sub.2 C.sub.6 H.sub.5            4-F, 3-cyclopentyloxy            4-F, 3-cyclohexyloxy            4-CH.sub.3, 3-OCH.sub.3            4-CH.sub.3, 3-OCH.sub.2 CH.sub.3            4-CH.sub.3, 3-OCH.sub.2 CH.sub.2 CH.sub.3            4-CH.sub.3, 3-OCH(CH.sub.3).sub.2            4-CH.sub.3, 3-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            4-CH.sub.3, 3-OCH(CH.sub.3)CH.sub.2 CH.sub.3            4-CH.sub.3, 3-OCH.sub.2 CH(CH.sub.3).sub.2            4-CH.sub.3, 3-OC(CH.sub.3).sub.3            4-CH.sub.3, 3-OCF.sub.3            4-CH.sub.3, 3-OCF.sub.2 Br            4-CH.sub.3, 3-OCF.sub.2 H            4-CH.sub.3, 3-OCF.sub.2 CF.sub.2 H            4-CH.sub.3, 3-OCF.sub.2 CFHCF.sub.3            4-CH.sub.3, 3-OCH.sub.2 CF.sub.3            4-CH.sub.3, 3-OC.sub.6 H.sub.5            4-CH.sub.3, 3-OCH.sub.2 C.sub.6 H.sub.5            4-CH.sub.3, 3-cyclopentyloxy            4-CH.sub.3, 3-cyclohexyloxy            2-Cl, 5-OCH.sub.3            2-Cl, 5-OCH.sub.2 CH.sub.3            2-Cl, 5-OCH.sub.2 CH.sub.2 CH.sub.3            2-Cl, 5-OCH(CH.sub.3).sub.2            2-Cl, 5-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            2-Cl, 5-OCH(CH.sub.3)CH.sub.2 CH.sub.3            2-Cl, 5-OCH.sub.2 CH(CH.sub.3).sub.2            2-Cl, 5-OC(CH.sub.3).sub.3            2-Cl, 5-OCF.sub.3            2-Cl, 5-OCF.sub.2 Br            2-Cl, 5-OCF.sub.2 H            2-Cl, 5-OCF.sub.2 CF.sub.2 H            2-Cl, 5-OCF.sub.2 CFHCF.sub.3            2-Cl, 5-OCH.sub.2 CF.sub.3            2-Cl, 5-OC.sub.6 H.sub.5            2-Cl, 5-OCH.sub.2 C.sub.6 H.sub.5            2-Cl, 5-cyclopentyloxy            2-Cl, 5-cyclohexyloxy            2-Cl, 4-OCH.sub.3            2-Cl, 4-OCH.sub.2 CH.sub.3            2-Cl, 4-OCH.sub.2 CH.sub.2 CH.sub.3            2-Cl, 4-OCH(CH.sub.3).sub.2            2-Cl, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            2-Cl, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3            2-Cl, 4-OCH.sub.2 CH(CH.sub.3).sub.2            2-Cl, 4-OC(CH.sub.3).sub.3            2-Cl, 4-OCF.sub.3            2-Cl, 4-OCF.sub.2 Br            2-Cl, 4-OCF.sub.2 H            2-Cl, 4-OCF.sub.2 CF.sub.2 H            2-Cl, 4-OCF.sub.2 CFHCF.sub.3            2-Cl, 4-OCH.sub.2 CF.sub.3            2-Cl, 4-OC.sub.6 H.sub.5            2-Cl, 4-OCH.sub.2 C.sub.6 H.sub.5            2-Cl, 4-cyclopentyloxy            2-Cl, 4-cyclohexyloxy            4-OCH.sub.3, 3-OCH.sub.2 CH.sub.2 CH.sub.3            4-OCH.sub.3, 3-OCH(CH.sub.3).sub.2            4-OCH.sub.3, 3-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            4-OCH.sub.3, 3-OCH(CH.sub.3)CH.sub.2 CH.sub.3            4-OCH.sub.3, 3-OCH.sub.2 CH(CH.sub.3).sub.2            4-OCH.sub.3, 3-OC(CH.sub.3).sub.3            4-OCH.sub.3, 3-OCF.sub.3            4-OCH.sub.3, 3-OCF.sub.2 Br            4-OCH.sub.3, 3-OCF.sub.2 H            4-OCH.sub.3, 3-OCF.sub.2 CF.sub.2 H            4-OCH.sub.3, 3-OCF.sub.2 CFHCF.sub.3            4-OCH.sub.3, 3-OCH.sub.2 CF.sub.3            4-OCH.sub.3, 3-OC.sub.6 H.sub.5            4-OCH.sub.3, 3-OCH.sub.2 C.sub.6 H.sub.5            4-OCH.sub.3, 3-cyclopentyloxy            4-OCH.sub.3, 3-cyclohexyloxy            2,5-(CH.sub.3).sub.2, 4-OCH.sub.3            2,5-(CH.sub.3).sub.2, 4-OCH.sub.2 CH.sub.3            2,5-(CH.sub.3).sub.2, 4-OCH.sub.2 CH.sub.2 CH.sub.3            2,5-(CH.sub.3).sub.2, 4-OCH(CH.sub.3).sub.2            2,5-(CH.sub.3).sub.2,            4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            2,5-(CH.sub.3).sub.2,            4-OCH(CH.sub.3)CH.sub.2 CH.sub.3            2,5-(CH.sub.3).sub.2,            4-OCH.sub.2 CH(CH.sub.3).sub.2            2,5-(CH.sub.3).sub.2, 4-OC(CH.sub.3).sub.3            2,5-(CH.sub.3).sub.2, 4-OCF.sub.3            2,5-(CH.sub.3).sub.2, 4-OCF.sub.2 Br            2,5-(CH.sub.3).sub.2, 4-OCF.sub.2 H            2,5-(CH.sub.3).sub.2, 4-OCF.sub.2 CF.sub.2 H            2,5-(CH.sub.3).sub.2, 4-OCF.sub.2 CFHCF.sub.3            2,5-(CH.sub.3).sub.2, 4-OCH.sub.2 CF.sub.3            2,5-(CH.sub.3).sub.2, 4-OC.sub.6 H.sub.5            2,5-(CH.sub.3).sub.2, 4-OCH.sub.2 C.sub.6 H.sub.5            2,5-(CH.sub.3).sub.2, 4-cyclopentyloxy            2,5-(CH.sub.3).sub.2, 4-cyclohexyloxy            3,5-(CH.sub.3).sub.2, 4-OCH.sub.3            3,5-(CH.sub.3).sub.2, 4-OCH.sub.2 CH.sub.3            3,5-(CH.sub.3).sub.2, 4-OCH.sub.2 CH.sub.2 CH.sub.3            3,5-(CH.sub.3).sub.2, 4-OCH(CH.sub.3).sub.2            3,5-(CH.sub.3).sub.2,            4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            3,5-(CH.sub.3).sub.2,            4-OCH(CH.sub.3)CH.sub.2 CH.sub.3            3,5-(CH.sub.3).sub.2,            4-OCH.sub.2 CH(CH.sub.3).sub.2            3,5-(CH.sub.3).sub.2, 4-OC(CH.sub.3).sub.3            3,5-(CH.sub.3).sub.2, 4-OCF.sub.3            3,5-(CH.sub.3).sub.2, 4-OCF.sub.2 Br            3,5-(CH.sub.3).sub.2, 4-OCF.sub.2 H            3,5-(CH.sub.3).sub.2, 4-OCF.sub.2 CF.sub.2 H            3,5-(CH.sub.3).sub.2, 4-OCF.sub.2 CFHCF.sub.3            3,5-(CH.sub.3).sub.2, 4-OCH.sub.2 CF.sub.3            3,5-(CH.sub.3).sub.2, 4-OC.sub.6 H.sub.5            3,5-(CH.sub.3).sub.2, 4-OCH.sub.2 C.sub.6 H.sub.5            3,5-(CH.sub.3).sub.2, 4-cyclopentyloxy            3,5-(CH.sub.3).sub.2, 4-cyclohexyloxy            3,5-Cl.sub.2, 4-OCH.sub.3            3-OC.sub.6 H.sub.4 (p-F)            3,5-Cl.sub.2, 4-OCH.sub.2 CH.sub.3            3,5-Cl.sub.2, 4-OCH.sub.2 CH.sub.2 CH.sub.3            3,5-Cl.sub.2, 4-OCH(CH.sub.3).sub.2            3 5-Cl.sub.2, 4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3            3,5-Cl.sub.2, 4-OCH(CH.sub.3)CH.sub.2 CH.sub.3            3,5-Cl.sub.2, 4-OCH.sub.2 CH(CH.sub.3).sub.2            3,5-Cl.sub.2, 4-OC(CH.sub.3).sub.3            3,5-Cl.sub.2, 4-OCF.sub.3            3,5-Cl.sub.2, 4-OCF.sub.2 Br            3,5-Cl.sub.2, 4-OCF.sub.2 H            3,5-Cl.sub.2, 4-OCF.sub.2 CF.sub.2 H            3,5-Cl.sub.2, 4-OCF.sub.2 CFHCF.sub.3            3,5-Cl.sub.2, 4-OCH.sub.2 CF.sub.3            3,5-Cl.sub.2, 4-OC.sub.6 H.sub.5            3,5-Cl.sub.2, 4-OCH.sub.2 C.sub.6 H.sub.5            3,5-Cl.sub.2, 4-cyclopentyloxy            3,5-Cl.sub.2, 4-cyclohexyloxy            2-F, 5-OC.sub.6 H.sub.4 (p-F)            2-Br, 5-(OC.sub.6 H.sub.5)            4-(OC.sub.6 H.sub.4 p-CF.sub.3)            3-OC.sub.6 H.sub.4 (p-F)            4-OH            3-SF.sub.5            4-SF.sub.5            2,3,4-Cl.sub.3            2,5,6-Cl.sub.3            2,4,5-Cl.sub.3            2,3,4,6-Cl.sub.4            3,4-OCF.sub.2 O            2,6-Cl.sub.2, 4-OCH.sub.2 CHC(Cl).sub.2            4-C.sub.6 H.sub.4 -(p-OCF.sub.3)     ______________________________________

                  TABLE 13     ______________________________________      ##STR141##      ##STR142##      ##STR143##      ##STR144##      ##STR145##      ##STR146##      ##STR147##      ##STR148##      ##STR149##      ##STR150##      ##STR151##      ##STR152##      ##STR153##      ##STR154##      ##STR155##      ##STR156##      ##STR157##      ##STR158##      ##STR159##      ##STR160##      ##STR161##      ##STR162##      ##STR163##      ##STR164##      ##STR165##      ##STR166##      ##STR167##      ##STR168##      ##STR169##      ##STR170##      ##STR171##      ##STR172##      ##STR173##      ##STR174##      ##STR175##      ##STR176##      ##STR177##     ((R.sup.9)l in Table 13 is as defined below.)              (R.sup.9)l     ______________________________________              H              2-F              2-CF.sub.3              2-Cl              2-Br              2-I              2-OCH.sub.3              2-OCH.sub.2 CH.sub.3              2-CN              3-CH.sub.3              3-F              3-CF.sub.3              3-Cl              3-Br              3-I              3-OCH.sub.3              3-OC.sub.6 H.sub.5              3-OCH.sub.2 C.sub.6 H.sub.5              3-OCF.sub.3              3-OCF.sub.2 CF.sub.2 H              3-NO.sub.2              3-OC.sub.6 H.sub.4 (p-CH.sub.3)              3-OC.sub.6 H.sub.4 (p-C(CH.sub.3).sub.3)              3-OC.sub.6 H.sub.4 (m-CF.sub.3)              3-OC.sub.6 H.sub.4 (p-Cl)              3-OC.sub.6 H.sub.4 (3,4-Cl.sub.2)              3-OC.sub.6 H.sub.3 (3,5-Cl.sub.2)              3-OC.sub.6 H.sub.4 (p-OCH.sub.3)              3-CN              3-CH.sub.3              3-CH.sub.2 CH.sub.3              3-CH.sub.2 CH.sub.2 CH.sub.3              3-CH(CH.sub.3).sub.2              3-C(CH.sub.3).sub.3              3-OCF.sub.2 Br              3-OCF.sub.2 H              3-OCF.sub.2 CFHCF.sub.3              3-OCH.sub.2 CF.sub.3              3-OCH.sub.2 CH.sub.3              3-OCH.sub.2 CH.sub.2 CH.sub.3              3-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3              3-OCH(CH.sub.3).sub.2              3-OCH(CH.sub.3)CH.sub.2 CH.sub.3              3-OCH.sub.2 CH(CH.sub.3)CH.sub.3              3-OC(CH.sub.3).sub.3              3-OCH.sub.2 CHCH.sub.2              3-OCH.sub.2 CHC(Cl).sub.2              3-OCH.sub.2 CHC(Br).sub.2              3-OCH.sub.2 CHCH(Cl)              3-OCH.sub.2 C(Cl)CH(Cl)              3-OCH.sub.2 CHC(CH.sub.3).sub.2              3-OCH.sub.2 CHCH(CH.sub.3)              3-OCH.sub.2 C(CH.sub.3)CH.sub.2              3-OCH.sub.2 CBrCH(Br)              3-OCH.sub.2 C CH              3-OCH.sub.2 C CCl              3-OCH.sub.2 C CBr              3-OCH.sub.2 C CCH.sub.3              3-OCH(CH.sub.3)CCH              3-cyclopentyl              3-cyclohexyl              3-(3-cyclopentenyl)              3-(4-cyclopentenyl)               ##STR178##               ##STR179##               ##STR180##               ##STR181##               ##STR182##              3-cyclopropyloxy              3-cyclobutyloxy              3-cyclopentyloxy              3-cyclohexyloxy              3-(3-cyclohexenyl)              3-(4-cyclohexenyl)              3-(5-cyclohexenyl)              3-(3-cyclopentenyloxy)              3-(4-cyclopentenyloxy)              3-(3-cyclohexenyloxy)              3-(4-cyclohexenyloxy)              3-(5-cyclohexenyloxy)              3-CH.sub.2 C.sub.6 H.sub.5              3-OCH.sub.2 CHC(Cl)(CH.sub.3)              3-OCH.sub.2 CHC(CH.sub.3)(CF.sub.3)              3-OC.sub.6 H.sub.4 (o-Cl)              3-OC.sub.6 H.sub.4 (o-F)              3-OC.sub.6 H.sub.4 (o-CH.sub.3)              3-OC.sub.6 H.sub.4 (o-Cl)              3-OC.sub.6 H.sub.4 (m-F)              3-OC.sub.6 H.sub.4 (m-CH.sub.3)              3-OCH.sub.2 C.sub.6 H.sub.4 (o-Cl)              3-OCH.sub.2 C.sub.6 H.sub.4 (o-F)              3-OCH.sub.2 C.sub.6 H.sub.4 (o-Br)              3-OCH.sub.2 C.sub.6 H.sub.4 (o-CH.sub.3)              3-OCH.sub.2 C.sub.6 H.sub.4 (o-CF.sub.3)              3-OCH.sub.2 C.sub.6 H.sub.4 (m-Cl)              3-OCH.sub.2 C.sub.6 H.sub.4 (m-F)              3-OCH.sub.2 C.sub.6 H.sub.4 (m-Br)              3-OCH.sub.2 C.sub.6 H.sub.4 (m-CH.sub.3)              3-OCH.sub.2 C.sub.6 H.sub.4 (m-CF.sub.3)              3-OCH.sub.2 C.sub.6 H.sub.4 (p-Cl)              3-OCH.sub.2 C.sub.6 H.sub.4 (p-Br)              3-OCH.sub.2 C.sub.6 H.sub.4 (p-F)              3-OCH.sub.2 C.sub.6 H.sub.4 (p-CH.sub.3)              3-OCH.sub.2 C.sub.6 H.sub.4 (p-CF.sub.3)              3-SCF.sub.2 CF.sub.2 H              3-SCH.sub.3              3-SCH.sub.2 CH.sub.3              3-OCH.sub.2 C(Cl)CH.sub.2              4-CH.sub.3              4-CH.sub.2 CH.sub.3              4-CH(CH.sub.3).sub.2              4-C(CH.sub.3).sub.3              4-CH.sub.2 (CH.sub.2).sub.2 CH.sub.3              4-F              4-CF.sub.3              4-Cl              4-Br              4-OCH.sub.3              4-OCH.sub.2 CH.sub.3              4-OCH.sub.2 (CH.sub.2).sub.2 CH.sub.3              4-OCF.sub.3              4-C.sub.6 H.sub.5              4-OCH.sub.2 C.sub.6 H.sub.5              4-OCH.sub.2 CH.sub.2 CH.sub.3              4-OCF.sub.3              4-SCH.sub.3              4-NO.sub.2              4-OC.sub.6 H.sub.5              4-CH.sub.2 (CH.sub.2).sub.3 CH.sub.3              4-CH.sub.2 (CH.sub.2).sub.4 CH.sub.3              4-CH.sub.2 (CH.sub.2).sub.5 CH.sub.3              4-CH.sub.2 (CH.sub.2).sub.6 CH.sub.3              4-CHCH.sub.2              4-I              4-OCH.sub.2 (CH.sub.2).sub.3 CH.sub.3              4-OCH.sub.2 (CH.sub.2).sub.4 CH.sub.3              4-OCH.sub.2 (CH.sub.2).sub.5 CH.sub.3              4-OCH(CH.sub.3).sub.2              4-(2-cyclohexenyl)              4-SCH.sub.2 CH.sub.3              4-C.sub.6 H.sub.4 (p-CH.sub.2 CH.sub.3)              4-CN              4-OCF.sub.2 Br              4-OCF.sub.2 H              4-OCF.sub.2 CFHCF.sub.3              4-OCH.sub.2 CF.sub.3              4-OCF.sub.2 CF.sub.2 H              4-SCF.sub.2 CF.sub.2 H              4-SCH(CH.sub.3).sub.2              4-OCH.sub.2 CHCH.sub.2              4-OCH.sub.2 CHC(Cl).sub.2              4-OCH.sub.2 CHC(Br).sub.2              4-OCH.sub.2 CHCH(Cl)              4-OCH.sub.2 C(Cl)CH(Cl)              4-OCH.sub.2 CHC(CH.sub.3).sub.2              4-OCH.sub.2 CHCH(CH.sub.3)              4-OCH.sub.2 C(CH.sub.3)CH.sub.2              4-OCH.sub.2 C(Cl)CH.sub.2              4-OCH.sub.2 C(Br)CH.sub.2 (Br)              4-OCH.sub.2 C CH              4-OCH.sub.2 C CCl              4-OCH.sub.2 C CBr              4-OCH.sub.2 C CCH.sub.3              4-OCH(CH.sub.3)CCH              4-cyclopentyl              4-cyclohexyl              4-(3-cyclopentenyl)              4-(4-cyclopentenyl)               ##STR183##               ##STR184##               ##STR185##               ##STR186##               ##STR187##              4-cyclopropyloxy              4-cyclobutyloxy              4-cyclopentyloxy              4-cyclohexyloxy              4-(3-cyclohexenyl)              4-(4-cyclohexenyl)              4-(5-cyclohexenyl)              4-(3-cyclopentenyloxy)              4-(4-cyclopentenyloxy)              4-(3-cyclohexenyloxy)              4-(4-cyclohexenyloxy)              4-(5-cyclohexenyloxy)              4-CH.sub.2 C.sub.6 H.sub.5              4-OCH.sub.2 CHC(Cl)CH.sub.3              4-OCH.sub.2 CHC(CH.sub.3)CF.sub.3              4-OC.sub.6 H.sub.4 (o-Cl)              4-OC.sub.6 H.sub.4 (o-F)              4-OC.sub.6 H.sub.4 (o-CH.sub.3)              4-OC.sub.6 H.sub.4 (m-Cl)              4-OC.sub.6 H.sub.4 (m-F)              4-OC.sub.6 H.sub.4 (m-CH.sub.3)              4-OCH.sub.2 C.sub.6 H.sub.4 (o-Cl)              4-OCH.sub.2 C.sub.6 H.sub.4 (o-F)              4-OCH.sub.2 C.sub.6 H.sub.4 (o-Br)              4-OCH.sub.2 C.sub.6 H.sub.4 (o-CH.sub.3)              4-OCH.sub.2 C.sub.6 H.sub.4 (o-CF.sub.3)              4-OCH.sub.2 C.sub.6 H.sub.4 (m-Cl)              4-OCH.sub.2 C.sub.6 H.sub.4 (m-F)              4-OCH.sub.2 C.sub.6 H.sub.4 (m-Br)              4-OCH.sub.2 C.sub.6 H.sub.4 (m-CH.sub.3)              4-OCH.sub.2 C.sub.6 H.sub.4 (m-CF.sub.3)              4-OCH.sub.2 C.sub.6 H.sub.4 (p-Cl)              4-OCH.sub.2 C.sub.6 H.sub.4 (p-Br)              4-OCH.sub.2 C.sub.6 H.sub.4 (p-F)              4-OCH.sub.2 C.sub.6 H.sub.4 (p-CH.sub.3)              4-OCH.sub.2 C.sub.6 H.sub.4 (p-CF.sub.3)              4-SCF.sub.2 CF.sub.2 H              4-OCH.sub.2 C(Cl)CH.sub.2              4-F, 3-OC.sub.6 H.sub.5              4-F, 3-OCH.sub.2 C.sub.6 H.sub.5              4-Cl, 3-OC.sub.6 H.sub.5              4-Cl, 3-OCH.sub.2 C.sub.6 H.sub.5              4-CH.sub.3, 3-OC.sub.6 H.sub.5              4-CH.sub.3, 3-OCH.sub.2 C.sub.6 H.sub.5              4-Br, 3-OCH.sub.2 C.sub.6 H.sub.5              3-F, 3-OC.sub.6 H.sub.5              3-Cl, 4-OC.sub.6 H.sub.5              3-CH.sub.3, 4-OC.sub.6 H.sub.5              3-F, 4-OCH.sub.2 C.sub.6 H.sub.5              3-Cl, 4-OCH.sub.2 C.sub.6 H.sub.5              3-Br, 4-OCH.sub.2 C.sub.6 H.sub.5              3-CH.sub.3, 4-OCH.sub.2 C.sub.6 H.sub.5     ______________________________________

                  TABLE 14     ______________________________________      ##STR188##              (R.sup.9)l     ______________________________________              H              3-F              3-CF.sub.3              3-Cl              3-Br              3-OC.sub.6 H.sub.5              3-OCH.sub.2 C.sub.6 H.sub.5              4-F, 3-OC.sub.6 H.sub.5              4-F, 3-OCH.sub.2 C.sub.6 H.sub.5              4-Cl, 3-OC.sub.6 H.sub.5              4-Cl, 3-OCH.sub.2 C.sub.6 H.sub.5              4-CH.sub.3, 3-OC.sub.6 H.sub.5              4-CH.sub.3, 3-OCH.sub.2 C.sub.6 H.sub.5              4-Br, 3-OCH.sub.2 C.sub.6 H.sub.5              3-F, 4-OC.sub.6 H.sub.5              3-F, 4-OCH.sub.2 C.sub.6 H.sub.5              3-Cl, 4-OC.sub.6 H.sub.5              3-Cl, 4-OCH.sub.2 C.sub.6 H.sub.5              3-CH.sub.3, 4-OC.sub.6 H.sub.5              3-CH.sub.3, 4-OCH.sub.2 C.sub.6 H.sub.5              3-Br, 4-OCH.sub.2 C.sub.6 H.sub.5              3-cyclohexyl              3-cyclopentyl              3-cyclohexyloxy              3-cyclopentyloxy              4-cyclohexyl              4-cyclopentyl              4-cyclohexyloxy              4-cyclopentyloxy              4-F              4-CF.sub.3              4-Cl              4-Br              4-OC.sub.6 H.sub.5              4-OCH.sub.2 C.sub.6 H.sub.5              3-OCH.sub.2 CHC(Cl).sub.2              3-OCH.sub.2 CHC(Br).sub.2              4-OCH.sub.2 CHC(Cl).sub.2              4-OCH.sub.2 CHC(Br).sub.2              3-Cl, 4-OCH.sub.2 CHC(Cl).sub.2              3-Cl, 4-OCH.sub.2 CHC(Br).sub.2     ______________________________________

                  TABLE 15     ______________________________________      ##STR189##               (R.sup.9)l     ______________________________________               H               3-F               3-CF.sub.3               3-Cl               3-Br               3-OC.sub.6 H.sub.5               3-OCH.sub.2 C.sub.6 H.sub.5               4-F, 3-OC.sub.6 H.sub.5               4-F, 3-OCH.sub.2 C.sub.6 H.sub.5               4-Cl, 3-OC.sub.6 H.sub.5               4-Cl, 3-OCH.sub.2 C.sub.6 H.sub.5               4-CH.sub.3, 3-OC.sub.6 H.sub.5               4-CH.sub.3, 3-OCH.sub.2 C.sub.6 H.sub.5               4-Br, 3-OCH.sub.2 C.sub.6 H.sub.5               3-F, 4-OC.sub.6 H.sub.5               3-F, 4-OCH.sub.2 C.sub.6 H.sub.5               3-Cl, 4-OC.sub.6 H.sub.5               3-Cl, 4-OCH.sub.2 C.sub.6 H.sub.5               3-CH.sub.3, 4-OC.sub.6 H.sub.5               3-CH.sub.3, 4-OCH.sub.2 C.sub.6 H.sub.5               3-Br, 4-OCH.sub.2 C.sub.6 H.sub.5               3-cyclohexyl               3-cyclopentyl               3-cyclohexyloxy               3-cyclopentyloxy               4-cycylohexyl               4-cyclopentyl               4-cyclohexyloxy               4-cyclopentyloxy               4-F               4-CF.sub.3               4-Cl               4-Br               4-OC.sub.6 H.sub.5               4-OCH.sub.2 C.sub.6 H.sub.5               3-OCH.sub.2 CHC(Cl).sub.2               3-OCH.sub.2 CHC(Br).sub.2               4-OCH.sub.2 CHC(Cl).sub.2               4-OCH.sub.2 CHC(Br).sub.2               3-Cl, 4-OCH.sub.2 CHC(Cl).sub.2               3-Cl, 4-OCH.sub.2 CHC(Br).sub.2     ______________________________________

                  TABLE 16     ______________________________________      ##STR190##               (R.sup.9)l     ______________________________________               H               3-F               3-CF.sub.3               3-Cl               3-Br               3-OC.sub.6 H.sub.5               3-OCH.sub.2 C.sub.6 H.sub.5               4-F, 3-OC.sub.6 H.sub.5               4-F, 3-OCH.sub.2 C.sub.6 H.sub.5               4-Cl, 3-OC.sub.6 H.sub.5               4-Cl, 3-OCH.sub.2 C.sub.6 H.sub.5               4-CH.sub.3, 3-OC.sub.6 H.sub.5               4-CH.sub.3, 3-OCH.sub.2 C.sub.6 H.sub.5               4-Br, 3-OCH.sub.2 C.sub.6 H.sub.5               3-F, 4-OC.sub.6 H.sub.5               3-F, 4-OCH.sub.2 C.sub.6 H.sub.5               3-Cl, 4-OC.sub.6 H.sub.5               3-Cl, 4-OCH.sub.2 C.sub.6 H.sub.5               3-CH.sub.3, 4-OC.sub.6 H.sub.5               3-CH.sub.3, 4-OCH.sub.2 C.sub.6 H.sub.5               3-Br, 4-OCH.sub.2 C.sub.6 H.sub.5               3-cyclohexyl               3-cyclopentyl               3-cyclohexyloxy               3-cyclopentyloxy               4-cycylohexyl               4-cyclopentyl               4-cyclohexyloxy               4-cyclopentyloxy               4-F               4-CF.sub.3               4-Cl               4-Br               4-OC.sub.6 H.sub.5               4-OCH.sub.2 C.sub.6 H.sub.5               3-OCH.sub.2 CHC(Cl).sub.2               3-OCH.sub.2 CHC(Br).sub.2               4-OCH.sub.2 CHC(Cl).sub.2               4-OCH.sub.2 CHC(Br).sub.2               3-Cl, 4-OCH.sub.2 CHC(Cl).sub.2               3-Cl, 4-OCH.sub.2 CHC(Br).sub.2     ______________________________________

                                      TABLE 17     __________________________________________________________________________      ##STR191##     (R.sup.4).sub.m          (R.sup.12).sub.a               ##STR192##  A  p   R.sup.7                                    R.sup.10                                       R.sup.11     __________________________________________________________________________     H    H   1            0  1   H H  H     H    H   2            0  1   H H  H     H    H   1            0  2   H H  H     H    H   2            0  2   H H  H     H    H   1            0  3   H H  H     H    H   2            0  3   H H  H     H    H   1            0  4   H H  H     H    H   2            0  4   H H  H     H    H   1            NH 2   H H  H     H    H   2            NH 3   H H  H     H    H   1            S  2   H H  H     H    H   2            S  3   H H  H     __________________________________________________________________________

The aldehyde compound of the general formula X!, which is an intermediate for use in the production of the present compounds, can be produced, for example, according to the following scheme: ##STR193## wherein all variables are as defined above.

The compounds of the general formula IV!, V! or VI!, which are intermediate for use in the production of the present compounds, can be produced, for example, according to the following scheme: ##STR194## wherein R¹ is C₁ -C₁₀ alkyl, C₁ -C₅ haloalkyl, C₂ -C₁₀ alkenyl, C₂ -C₆ haloalkenyl, C₃ -C₉ alkynyl, C₃ -C₅ haloalkynyl, C₂ -C₇ alkoxyalkyl, C₂ -C₇ alkylthioalkyl; C₃ -C₆ cycloalkyl which may be substituted with C₁ -C₄ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; C₄ -C₉ cycloalkylalkyl which may be substituted with C₁ -C₄ alkyl; or C₆ -C₈ cycloalkenylalkyl which may be substituted with C₁ -C₄ alkyl, and R², R³, R¹⁴, r and L are each as defined above. ##STR195##

The compounds of the general formula III! or X!, which are intermediates for use in the production of the present compound, can be produced, for example, according to the following scheme: ##STR196##

The compounds of the general formula II!, XIII! or XIV!, which are intermediates for use in the production of the present compound, can be produced, for example, according to the following scheme: ##STR197## wherein the general formula XIV! represents the compound II! wherein L¹ is OH when r is 0, the general formula XIII! represents the compound II! wherein L¹ is L when r is 0, R²¹ is a protecting group (e.g., benzoyl) for alcohols, Ms is mesyl, Ts is tosyl, and other variables are each as defined above. ##STR198## wherein the produced compounds are the compound XIII! or XIV! wherein R⁷, R¹⁰ and R¹¹ are all hydrogen and the compound II! wherein r is 0, and all the variables are each as defined above.

The compound of the general formula VII! and the alcohol compound of the general formula VIII!, which are intermediates for use in the production of the present compounds, are commercially available or can be produced, for example, according to the following scheme: ##STR199## wherein L² is chlorine or bromine, L³ is mesyloxy or tosyloxy, and X is as defined above.

The present compounds are satisfactory effective for the control of various noxious insects, mites and ticks, examples of which are as follows:

Hemiptera

Delphacidae such as Laodelphax striatellus, Nilaparvata lugens and Sogatella furcifera, Deltocephalidae such as Nephotettix cincticeps and Nephotettix virescens, Aphididae, Pentatomidae, Aleyrodidae, Coccidae, Tingidae, Psyllidae, etc.

Lepidoptera

Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinalis, Ostrinia nubilalis, Parapediasia teterrella, Notarcha derogata and Plodia interpunctella, Noctuidae such as Spodoptera litura, Spodoptera exigua, Spodoptera litoralis, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon, Trichoplusia spp., Heliothisspp., Helicoverpa spp. and Earias spp., Pieridae such as Pieris rapae crucivora, Tortricidae such as Adoxophyes spp., Grapholita molesta and Cydia pomonella, Carposinidae such as Carposina niponensis, Lyonetiidae such as Lyonetia spp., Lymantriidae such as Lymantria spp. and Euproctis spp., Yponomeutidae such as Plutella xylostella, Gelechiidae such as Pectinophora gossypiella, Arctiidae such as Hyphantria cunea, Tineidae such as Tinea translucens and Tineola bisselliella, etc.

Diptera

Culex such as Culex pipiens pallens and Cules tritaeniorhynchus, Aedes such as Aedes albopictus and Aedes aegypti, Anopheles such as Anophelinae sinensis, Chironomidae, Muscidae such as Musca domestica and Muscina stabulans, Calliphoridae, Sarcophagidae, Fannia canicularis, Anthomyiidae such as Delia Platura and Delia antigua, Trypetidae, Drosophilidae, Psychodidae, Tabanidae, Simuliidae, Stomoxyinae, etc.

Coleoptera

Diabrotica such as Diabrotica virgifera and Diabrotica undecimpunctata, Scarabaeidae such as Anomala cuprea and Anomala rufocuprea, Curculionidae such as Lissorphoptrus oryzophilus, Hypera pastica, and Calosobruchys chinensis, Tenebrionidae such as Tenebrio molitor and Tribolium castaneum, Chrysomelidae such as Phyllotreta striolata and Aulacophora femoralis, Anobiidae, Epilachna spp. such as Henosepilachna vigintioctopunctata, Lyctidae, Bostrychidae, Cerambycidae, Paederus fuscipes, etc.

Dictyoptera

Blattella germanica, Periplaneta fuliginosa, Peroplaneta americana, Periplaneta brunnea, Blatta orientalis, etc.

Thysanoptera

Thrips palmi, Thrips hawaiiensis, etc.

Hymenoptera

Formicidae, Vespidae, Bethylidae, Tenthredinidae such as Athalia rosae japonensis, etc.

Orthoptera

Gryllotalpidae, Acrididae, etc.

Siphonaptera

Purex irritans, etc.

Anoplura

Pediculus humanus capitis, Phthirus pubis, etc.

Isoptera (termites)

Reticulitermes speratus, Coptotermes formosanus, etc.

Acarina

plant patasitic Tetranychidae such as Tetranychus uriticae, Panonychus citri, Tetranychus cinnabarinus and Panonychus ulmi, animal parasitic Ixodidae such as Boophilus microphus, house dust mites, etc.

The present compounds are also effective for the control of various noxious insects, mites and ticks having resistance to conventional insecticides and acaricides.

When the present compound is used as an active ingredient of insecticidal/acaricidal agents, it may be used as such without any addition of other ingredients. The present compound is, however, usually formulated into a dosage form such as oil sprays, emulsifiable concentrates, wettable powders, flowables, granules, dusts, aerosols, fumigants (foggings) and poison baits. These formulations are usually prepared by mixing the present compound with a solid carrier, a liquid carrier, a gaseous carrier or a bait, and if necessary, adding a surfactant and other auxiliaries used for formulation.

Each of the formulations usually contains the present compound as an active ingredient in an amount of 0.01% to 95% by weight.

Examples of the solid carrier to be used for the formulation are fine powder or granules of clay materials such as kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, Fubasami clay and acid clay; various kinds of talc, ceramics, other inorganic minerals such as sericite, quartz, sulfur, active carbon, calcium carbonate and hydrated silica; and chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride.

Examples of the liquid carrier are water; alcohols such as methanol and ethanol; ketones such as acetone and methyl ethyl ketone; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene and methylnaphthalene; aliphatic hydrocarbons such as hexane, cyclohexane, kerosine and gas oil; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and isobutyronitrile; ethers such as diisopropyl ether and dioxane; acid amides such as N,N-dimethylformamide and N,N-dimethylacetamide; halogenated hydrocarbons such as dichloromethane, trichloroethane and carbon tetrachloride; dimethyl sulfoxide; and vegetable oils such as soybean oil and cottonseed oil.

Examples of the gaseous carrier or propellant are flon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide.

Examples of the surfactant are alkyl sulfates, alkyl sulfonates, alkyl arylsulfonates, alkyl aryl ethers and their polyoxyethylene derivatives, polyethylene glycol ethers, polyhydric alcohol esters and sugar alcohol derivatives.

Examples of the auxiliaries used for formulation, such as fixing agents or dispersing agents, are casein, gelatin, polysaccharides such as starch, gum arabic, cellulose derivatives and alginic acid, lignin derivatives, bentonite, sugars, and synthetic water-soluble polymers such as polyvinyl alcohol, polyvinyl pyrrolidone and polyacrylic acid.

Examples of the stabilizer are PAP (isopropyl acid phosphate), BHT (2,6-di-tert-4-methylphenol), BHA (mixtures of 2-t-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, surfactants, fatty acids and their esters.

Examples of the base material to be used in the poison baits are bait materials such as grain powder, vegetable oils, sugars and crystalline cellulose; antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid; preservatives such as dehydroacetic acid; substances for preventing erroneous eating, such as red pepper powder, attractant flavors such as cheese flavor or onion flavor.

The formulation thus obtained is used as such or after diluted with water. The formulation may also be used in combination with other insecticides, nematocides, acaricides, bactericides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners and/or animal feed under non-mixing conditions or premixing conditions.

Examples of the insecticide, acaricide and/or nematocide which can be used are organophosphorus compounds such as Fenitrothion (O,O-dimethyl O-(3-methyl-4-nitrophenyl)phosphorothioate!, Fenthion O,O-dimethyl O-(3-methyl-4-methylthio)phenyl)phosphorothioate!, Diazinon O,O-diethyl-O-2-isopropyl-6-methylpyrimidin-4-ylphosphorothioate!, Chlorpyriphos O,O-diethyl-O-3,5,6-trichloro-2-pyridylphosphorothioate!, Acephate O,S-dimethylacetylphosphoramidothioate!, Methidachion S-2,3-dihydro-5-methoxy-2-oxo-1,3,4thiadiazol-3-ylmethyl O,O-dimethylphosphorodithioate!, Disulfotone O,O-diethyl S-2-ethylthioethylphosphorothioate!, DDVP 2,2-dichlorovinyldimethylphosphate!, Sulprofos O-ethyl O-4-(methylthio)phenyl S-propyl phosphorodithioate!, Cyanophos O-4-cyanophenyl O,O-dimethylphosphorothioate!, Dioxabenzofos 2-methoxy-4H-1,3,2-benzodioxaphosphinin-2-sulfide!, Dimethoate O,O-dimethyl-S-(N-methylcarbamoylmethyl)dithiophosphate!, Phenthoate ethyl 2-dimethoxyphosphinothioylthio(phenyl)acetate!, Malathion diethyl(dimethoxyphosphinothioylthio)succinate!, Trichlorfon dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate!, Azinphos-methyl S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl-O,O-dimethylphosphorodithioate!, Monocrotophos dimethyl (E)-1-methyl-2-(methylcarbamoyl)vinylphosphate!, Profenfos O-4-bromo-2-chlorophenyl O-ethyl S-propylphosphorothioate! and Ethion O,O,O',O'-tetraethyl S,S'-methylenebis(phosphorodithioate)!; carbamate compounds such as BPMC 2-sec-butylphenylmethylcarbamate!, Benfuracarb ethyl N- 2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio!-N-isopropyl-β-alaninate!, Propoxur 2-isopropoxyphenyl N-methylcarbamate!, Carbosulfan 2,3-dihydro-2,2-dimethyl-7-benzo b!-furanyl N-dibutylaminothio-N-methylcarbamate!, Carbaril 1-naphthyl-N-methylcarbamate!, Methomyl S-methyl-N- (methylcarbamoyl)oxy!thioacetoimidate!, Ethiofencarb 2-(ethylthiomethyl)phenylmethylcarbamate!, Aldicarb 2-methyl-2-(methylthio)propanaldehyde O-methylcarbamoyloxime!, Oxamyl N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide!, Thiodicarb 3,7,9,13-tetramethyl-5,11-dioxa-2,8,14-trithia-4,7,9,12-tetraazapentadeca-3,12-dien-6,10-dione!, Alanylcarb ethyl (Z)-N-benzyl-N-{ methyl(1-methylthioethylideneaminooxycarbonyl)amino!thio }-β-alanylate! and Fenothiocarb S-4phenoxybutyl)-N,N-dimethylthiocarbamate!; pyrethroid compounds such as Etofenprox 2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzylether!, Fenvalerate (RS)-α-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate!, Esfenvalerate (S)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate!, Fenpropathrin (RS)-α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate!, Cypermethrin (RS)-α-cyano-3-phenoxybenzyl (1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate!, Permethrin 3-phenoxybenzyl (1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate!, Cyhalothrin (RS)-α-cyano-3-phenoxybenzyl (Z)-(1RS,3RS)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate!, Deltamethrin (S)-α-cyano-m-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate!, Cycloprothrin (RS)-(α-cyano-3-phenoxybenzyl (RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate!, Fluvalinate α-cyano-3-phenoxybenzyl N-(2-chloro-α, α, α-trifluoro-p-tolyl)-D-valinate!, Bifenthrin 2-methylbiphenyl-3-ylmethyl)(Z)-(1RS)-cis -3-(2-chloro-3,3,3-trifluoropropen-1-yl)-2,2-dimethylcyclopropanecarboxylate!, Acrinathrin cyano-(3-phenoxyphenyl)methyl 1R-{1((S*),3α(Z)}!-2,2-dimethyl-3- 3-oxo-3-(2,2,2-trifluoro-1-(trifluoromethyl)-ethoxy 1-propenyl!cyclopropanecarboxylate!, 2-methyl-2-(4-bromodifluoromethoxyphenyl)propyl (3-phenoxybenzyl) ether, Traromethrin (S)-α-cyano-3-phenoxylbenzyl (1R, 3R)-3- (1'RS)(1',1',2'-tetrabromoethyl)!-2,2-dimethylcyclopropanecarboxylate! and Silafluofen 4-ethoxylphenyl 3-(4-fluoro-3-phenoxyphenyl)propyl!dimethylsilane!; thiadiazine derivatives such as Buprofezin 2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazin-4-one!; nitroimidazolidine derivatives such as Imidacloprid 1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylidenamine!; Nereistoxin derivatives such as Cartap S,S'-(2-dimethylaminotrimethylene)bisthiocarbamate!, Thiocyclam N,N-dimethyl-1,2,3-trithian-5-ylamine! and Bensultap S,S'-2-dimethylaminotrimethylene di(benzenethiosulfonate)!; N-cyanoamidine derivatives such as acetamiprid N-cyano-N'-methyl-N'-(6-chloro-3-pyridylmethyl)acetamidine!; chlorinated hydrocarbons such as Endosulfan 6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepinoxide!, γ-BHC 1,2,3,4,5,6-hexachlorocyclohexane! and Kelthane 1,1-bis-(chlorophenyl)-2,2,2-trichloroethanol!; benzoylphenylurea compounds such as Chlorfluazuron 1-(3,5-dichloro-4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl)-3-(2,6-difluorobenzoyl) urea!, Teflubenzuron 1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea! and Fulphenoxron 1-(4-(2-chloro-4-trifluoromethylphenoxy)-2-fluorophenyl)-3-(2,6-difluorobenzoyl)urea!; formamidine derivatives such as Amitraz N,N'- (methylimino)dimethylidine!-di-2,4-xylidine! and Chlordimeform N'-(4-chloro-2-methylphenyl)-N,N-dimethylmethanimidamide!; thiourea derivatives such as Diafenthiuron (N-(2,6-diisopropyl-4-phenoxyphenyl)-N'-tert-butylcarbodiimide!; Fipronyl 5-amino-1-(2,6-dichloro-α, α, α,-trifluoro -p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrite!, Tebfenozide N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide!, 4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethylpyrrole-3-carbonitrile, Chlorfenapyl 4-bromo-2-(4-chlorophenyl)-1-ethoxy methyl-S -trifluoromethylpyrole-3-carbonitril!, Bromopropylate isopropyl 4,4'-dibromobenzylate!, Tetradifon 4-chlorophenyl-2,4,5-trichlorophenyl sulfone!, Quinomethionate S,S-6-methylquinoxaline-2,3-diyldithiocarbonate!, Propargite 2-(4-tert-butylphenoxy)cyclohexyl prop-2-yl sulfite!, Fenbutatin oxide bis tris(2-methyl-2-phenylpropyl)tin)oxide!, Hexythiazox (4RS,5RS)-5-(4-chlorophenyl)-N-chlorohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide!, Chlofentezine 3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine!, Pyridaben 2-tert-butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H)-one!, Fenpyroximate tert-butyl(E)-4- (1,3-dimethyl-5-phenoxypyrazol-4-yl)methyleneaminooxymethyl!benzoate!, Tebfenpyrad N-4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methyl-5-pyrazol carboxamide!, polynactin complexes including tetranactin, trinactin and dinactin; Milbemectin, Avermectin, Ivermectin, Azadilactin AZAD!, Pyrimidifen 5-chloro-N- 2-{4-(2-ethoxyethyl)-2,3-dimethylphenoxy}ethyl!-6-ethylpyrimidin-4-amine! and Pimetrozine 2,3,4,5-tetrahydro-3-oxo-4- (pyridin-3-yl)-methyleneamino!-6-methyl-1,2,4-triazine!.

When the present compound is used as an active ingredient of insecticidal/acaricidal agents for agriculture, the application amount thereof is usually in the range of 0.1 to 100 g per 10 ares. In the case of emulsifiable concentrates, wettable powders and flowable concentrates, which are used after diluted with water, the application concentration thereof is usually in the range of 0.1 to 500 ppm. In the case of granules and dusts, they are applied as such without any dilution. When the present compound is used as an active ingredient of insecticidal/acaricidal agents for epidemic prevention, it is formulated into a dosage form such as emulsifiable concentrates, wettable powders and flowable concentrates, which are applied after diluted with water to a typical concentration of 0.1 to 500 ppm; or it is formulated into a dosage form such as oil sprays, aerosols, fumigants and poisonous baits, which are applied as such without any dilution.

The application amount and application concentration may vary depending upon various conditions such as formulation type, application time, place and method, kind of noxious insects, mites and ticks, and degree of damage, and they can be increased or decreased without limitation to the above range.

The present invention will be further illustrated by the following production examples, formulation examples and test examples, which are not to be construed to limit the scope thereof.

The following are production examples for the present compounds according to various production processes.

PRODUCTION EXAMPLE 1 Production of Compound (64) by Production Process E

To a solution of 0.30 g of 4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol, 0.16 g of 4-phenyl-1-butanol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.21 g of diethylazodicarboxylate dissolved in 5 ml of tetrahydrofuran was added dropwise, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.32 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-phenylbutyloxy)benzene (73% yield), n_(D) ²⁶.0 1.5716.

PRODUCTION EXAMPLE 2 Production of Compound (77) by Production Process E

To a solution of 0.30 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 0.16 g of 3-phenoxy-1-propanol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.21 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.36 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-phenoxypropyloxy)benzene (82% yield), n_(D) ²⁵.0 1.5762.

PRODUCTION EXAMPLE 3 Production of Compound (34) by Production Process B

To a solution of 0.33 g of 4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol, 0.23 g of m-phenoxybenzyl alcohol and 0.34 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.26 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was concentrated, and then mixed with 20 ml of diethyl ether. The precipitate was filtered, and the filtrate was concentrated. The residue was subjected to silica gel chromatography, which afforded 0.31 g of 3,5-dichloro-4-(3-phenoxybenzyl)-1-(3,3-dichloro-2-propenyloxy)-benzene (57% yield), n_(D) ²⁵.5 1.6066.

PRODUCTION EXAMPLE 4 Production of Compound (35) by Production Process E

To a solution of 0.46 g of 4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol, 0.32 g of p-phenoxybenzyl alcohol and 0.46 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.35 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was concentrated, and then mixed with 20 ml of diethyl ether. The precipitate was filtered, and the filtrate was concentrated. The residue was subjected to silica gel chromatography, which afforded 0.51 g of 3,5-dichloro-4-(4-phenoxybenzyl)-1-(3,3-dichloro-2-propenyloxy)benzene (68% yield), n_(D) ²⁵.5 1.6084.

PRODUCTION EXAMPLE 5 Production of Compound (63) by Production Process E

To a solution of 0.30 g of 4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol, 0.16 g of 4-chloro-β-phenetyl alcohol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.21 g of diethylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.32 g of 4-(4-chloro-β-phenetyloxy)-3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)benzene (72% yield), n_(D) ²⁴.5 1.5868.

PRODUCTION EXAMPLE 6 Production of Compound (1) by Production Process A

To a mixture of 600 mg of 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenol, 330 mg of potassium carbonate and 10 ml of N,N-dimethylformamide was added dropwise a solution of 340 mg of 1,1,3-trichloro-1-propene dissolved in 3 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring continued at room temperature for 5 hours, the reaction mixture was poured into ice-water, and extracted twice with 40 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 630 mg of 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene (82% yield), n_(D) ²⁴.6 1.5067.

PRODUCTION EXAMPLE 7 Production of Compound (41) by Production Process A

To a mixture of 1.10 g of 3,5-dichloro-4-(4-fluoro-3-phenoxy)benzyloxyphenol, 0.44 g of potassium carbonate and 20 ml of N,N-dimethylformamide was added dropwise a solution of 0.89 g of 1,1,3-tribromopropene dissolved in 5 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 7 hours, the reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 1.16 g of 3,5-dichloro-4-(4-fluoro-3-phenoxy)benzyloxy-1(3,3-dibromo-2-propenyloxy)benzene (69% yield), n_(D) ²².5 1.6062.

PRODUCTION EXAMPLE 8 Production of Compound (3) by Production Process B

To a solution of 0.54 g of 4-(3,3-dichloro-2-propenyloxy)-3,5-dichlorophenol, 0.24 g of 3,3-dichloroallyl alcohol and 0.49 g of triphenylphosphine dissolved in 15 ml of tetrahydrofuran was added dropwise a solution of 0.38 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.52 g of 4-(31(3,3-dichloro-2-propenyloxy)benzene (70% yield), m.p. 75.8° C.

PRODUCTION EXAMPLE 9 Production of Compound (47) by Production Process C

In a reaction vessel were placed 0.26 g of zinc dust, 1.0 g of triphenylphosphine, 1.3 g of carbon tetrabromide and 20 ml of methylene chloride, followed by stirring at room temperature. After 24 hours, a solution of 0.70 g of (4-(2-chlorobenzyloxy)-3,5-dichlorophenoxy)acetaldehyde dissolved in 5 ml of methylene chloride was added dropwise to the above solution, while stirring at room temperature. After stirring at room temperature for 6 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.63 g of 4-(2-chlorobenzyloxy)-3,5-dichloro-1-(3,3-dibromo-2-propenyloxy)benzene (63% yield), m.p. 83.5° C.

PRODUCTION EXAMPLE 10 Production of Compound (23) by Production Process D

To a mixture of 0.51 g of 2,6-dichloro-4-(3,3,-dichloro-2-propenyloxy)phenol, 0.27 g of potassium carbonate and 20 ml of N,N-dimethylformamide was added dropwise a solution of 0.29 g of m-chlorobenzyl chloride dissolved in 5 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 7 hours, the reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.50 g of 3,5-dichloro-4-(3-chlorobenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (69% yield), m.p. 87.0° C.

PRODUCTION EXAMPLE 11 Production of Compound (27) by Production Process D

To a mixture of 0.72 g of 2,6-dichloro-4-(3,3,-dichloro-2-propenyloxy)phenol, 0.38 g of potassium carbonate and 20 ml of N,N-dimethylformamide was added dropwise a solution of 0.71 g of 3-fluoro-4-phenoxybenzylbromide dissolved in 5 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 7 hours, the reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 1.05 g of 3,5-dichloro-4-(3-fluoro-4-phenoxy)benzyloxy-1-(3,3-dichloro-2-propenyloxy)benzene (86% yield), n_(D) ²².5 1.5973.

PRODUCTION EXAMPLE 12 Production of Compound (37) by Production Process E

To a solution of 0.41 g of 4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol, 0.17 g of (α-phenetyl alcohol and 0.37 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.29 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was concentrated, and then mixed with 20 ml of diethyl ether. The precipitate was filtered, and the filtrate was concentrated. The residue was subjected to silica gel chromatography, which afforded 0.27 g of 3,5-dichloro-4-α-phenetyloxy-1-(3,3-dichloro-2-propenyloxy)benzene (48% yield), n_(D) ²⁶.0 1.5830.

PRODUCTION EXAMPLE 13 Production of Compound (42) by Production Process E

To a solution of 0.30 g of 4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol, 0.12 g of P-phenetyl alcohol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.21 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was concentrated and mixed with 20 ml of diethyl ether. The precipitate was filtered, and the filtrate was concentrated. The residue was subjected to silica gel chromatography, which afforded 0.25 g of 3,5-dichloro-4-β-phenetyloxy-1-(3,3-dichloro-2-propenyloxy)benzene (61% yield), n_(D) ²⁸.5 1.5816.

PRODUCTION EXAMPLE 14 Production of Compound (19) by Production Process D

To a mixture of 0.51 g of 2,6-dichloro-4-(3,3,-dichloro-5-propenyloxy)phenol, 0.27 g of potassium carbonate and 20 ml of N,N-dimethylformamide was added dropwise a solution of 0.31 g of 2-(α-chloromethyl)naphthalene dissolved in 5 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 7 hours, the reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.58 g of 3,5-dichloro-4-(2-naphthylmethyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (76% yield), m.p. 86.7° C.

PRODUCTION EXAMPLE 15 Production of Compound (16) by Production Process D

To a mixture of 0.62 g of 2,6-dichloro-4-(3,3,-dichloro-2-propenyloxy)phenol, 0.33 g of potassium carbonate and 20 ml of N,N-dimethylformamide was added dropwise a solution of 0.43 g of cinnamyl bromide dissolved in 5 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 7 hours, the reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.70 g of 3,5-dichloro-4-(cinnamyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (80% yield), m.p. 51.3° C.

PRODUCTION EXAMPLE 16 Production of Compound (68) by Production Process D

To a mixture of 0.51 g of 2,6-dichloro-4-(3,3,-dichloro-2-propenyloxy)phenol, 0.17 g of potassium carbonate and 20 ml of N,N-dimethylformamide was added dropwise a solution of 0.34 g of 2-fluoro-5-(4-fluorophenoxy)benzyl bromide dissolved in 5 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.50 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-fluoro-5-(4-fluorophenoxy) benzyloxy)benzene (68% yield), n_(D) ²⁶.0 1.5871.

PRODUCTION EXAMPLE 17 Production of Compound (84) by Production Process E

To a solution of 0.30 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, phenol, 0.16 g of 3-chlorophenetyl alcohol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.21 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After siring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.36 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-(3-chlorophenyl)ethoxy)benzene (81% yield), n_(D) ²⁶.0 1.5897.

PRODUCTION EXAMPLE 18 Production of Compound (86) by Production Process E

To a solution of 0.30 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 0.20 g of 3-(trifluoromethyl)phenetyl alcohol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.21 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.39 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-(3-(trifluoromethyl) phenyl)ethoxy)benzene (81% yield), n_(D) ²⁶.0 1.5497.

PRODUCTION EXAMPLE 19 Production of Compound (91) by Production process E

A mixture of 1.14 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 1.20 g of 3-(4-chlorophenoxy)propyl bromide, 0.83 g of potassium carbonate and 20 ml of N,N-dimethylformamide was stirred at 80° C. for 6 hours. The reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 1.01 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-chlorophenoxy)propyloxy)benzene (55% yield), n_(D) ²⁵.0 1.5822.

PRODUCTION EXAMPLE 20 Production of Compound (99) by Production Process E

To a solution of 0.30 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 0.24 g of 3-(4-bromophenoxy)-1-propanol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.21 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.34 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-bromophenoxy) propyloxy)benzene (65% yield), n_(D) ²⁵.0 1.5917.

PRODUCTION EXAMPLE 21 Production of Compound (100) by Production Process E

To a solution of 0.30 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 0.25 g of 3-(4-trifluoromethoxy)phenoxy)-1-propanol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.21 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.41 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-(trifluoromethoxy) phenoxy)propyloxy)benzene (78% yield), n_(D) ²⁵.0 1.5342.

PRODUCTION EXAMPLE 22 Production of Compound (166) by Production Process F

A mixture of 0.56 g of 3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 0.22 g of 4-trifluoromethylphenol, 0.21 g of potassium carbonate and 20 ml of N,N-dimethylformamide was stirred at room temperature. After stirring for 7 hours, the reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.48 g of 3,5-dichloro-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (71% yield), n_(D) ²⁴.4 1.5390.

PRODUCTION EXAMPLE 23 Production of Compound (203) by Production Process F

A mixture of 0.88 g of 3,5-dichloro-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy) propenyloxy)benzene, 0.32 g of 4-isopropoxyphenol, 0.32 g of potassium carbonate and 20 ml of N,N-dimethylformamide was stirred at room temperature. After 7 hours, the reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.54 g of 3,5-dichloro-4-(4-(4-iso-propoxyphenoxy) butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (51% yield), n_(D) ²³.0 1.5578.

PRODUCTION EXAMPLE 24 Production of Compound (222) by Production Process F

A mixture of 0.61 g of 3,5-dichloro-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy) benzene, 0.19 g of 4-chlorophenol, 0.22 g of potassium carbonate and 20 ml of N,N-dimethylformamide was stirred at room temperature. After 7 hours, the reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.54 g of 3,5-dichloro-4-(4-(4-chlorophenoxy) butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (59% yield), m.p. 54.5° C.

PRODUCTION EXAMPLE 25 Production of Compound (152) by Production Process F

In a reaction vessel were placed 0.29 g of 3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 0.12 g of 4-ethoxybenzoic acid, 0.12 g of potassium carbonate and 10 ml of N,N-dimethylformamide, followed by stirring at room temperature for 12 hours. The reaction mixture was poured into water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.30 g of 3,5-dichloro-4-(3-(4-ethoxybenzoyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)-benzene (86% yield), n_(D) ²⁴.0 1.5715.

PRODUCTION EXAMPLE 26 Production of Compound (235) by Production Process F

In a reaction vessel were placed 0.20 g of 3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 0.10 g of 4-chlorophenylacetic acid, 0.08 g of potassium carbonate and 5 ml of N,N-dimethylformamide, followed by stirring at room temperature for 12 hours. The reaction mixture was poured into water, and extracted twice with 30 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.22 g of 3,5-dichloro-4-(3-(4-chlorophenylacetyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy) benzene (90% yield), n_(D) ²².0 1.5698.

PRODUCTION EXAMPLE 27 Production of Compound (236) by Production Process F

In a reaction vessel were placed 0.20 g of 3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 0.11 g of 4-chlorocinnamic acid, 0.08 g of potassium carbonate and 5 ml of N,N-dimethylformamide, followed by stirring at room temperature for 12 hours. The reaction mixture was poured into water, and extracted twice with 30 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.24 g of 3,5-dichloro-4-(3-(4-chlorophenylacetyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy) benzene (96% yield), m.p. 62.2° C.

PRODUCTION EXAMPLE 27 Production of Compound (237) by Production Process F

In a reaction vessel were placed 0.20 g of 3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 0.11 g of 4-chlorophenoxyacetic acid, 0.08 g of potassium carbonate and 5 ml of N,N-dimethylformamide, followed by stirring at room temperature for 12 hours. The reaction mixture was poured into water, and extracted twice with 30 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.23 g of 3,5-dichloro-4-(3-(4-chlorophenoxyacetyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy) benzene (91% yield), n_(D) ²².0 1.5709.

PRODUCTION EXAMPLE 29 Production of Compound (185) by Production Process G

To a solution of 1.10 g of 3,5-dichloro-4-(3-hydroxypropoxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 0.56 g of 3-trifluoromethoxyphenol and 0.83 g of triphenylphosphine dissolved in 20 ml of tetrahydrofuran was added dropwise a solution of 0.64 g of diisopropylazodicarboxylate dissolved in 10 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 1.03 g of 3,5-dichloro-4-(3-(4-trifluoromethoxyphenoxy) propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene (64% yield), n_(D) ²³.4 1.5343.

PRODUCTION EXAMPLE 30 Production of Compound (276) by Production Process F

A mixture of 3.9 g of 4-(trifluoromethyl)aniline and 0.50 g of 1-(3-bromopropyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene was stirred at 90° C. to 100° C. for 3 hours. After cooling to room temperature, the reaction mixture was subjected to silica gel chromatography, which afforded 0.37 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-(trifluoromethyl)phenylamino)propyloxy)benzene (62% yield), n_(D) ²³.5 1.5617.

PRODUCTION EXAMPLE 31 Production of Compound (277)

A mixture of 0.37 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-(trifluoromethyl) phenylamino)propyloxy)benzene, 0.1 ml of methyl iodide, 0.12 g of potassium carbonate and 10 ml of N,N-dimethylformamide was stirred at 50° C. for 3 hours. After cooling to room temperature, the reaction mixture was poured into ice-water, and extracted twice with 50 ml of ethyl acetate. The combined ethyl acetate layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.26 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(methyl(4-(trifluoromethyl)phenyl)amino)propyloxy)benzene (68% yield), n_(D) ²⁵.5 1.5593.

PRODUCTION EXAMPLE 32 Production of Compound (182) according to Production Process F

A mixture of 0.47 g of 4-chlorothiophenol, 1.33 g of 1-(3-bromopropyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene, 0.49 g of potassium carbonate and 20 ml of N,N-dimethylformamide was stirred at room temperature for 24 hours. The reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 1.24 g of 1-(3-(4-chlorophenylthio) propyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene (81% yield), n_(D) ²⁶.0 1.6035.

PRODUCTION EXAMPLE 33 Production of Compound (268)

A mixture of 0.50 g of 1-(3-(4-chlorophenylthio)propyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene and 20 ml of methylene chloride was stirred under cooling with ice-water, to which 0.26 g of m-chloroperbenzoic acid was added. After stirring at room temperature for 24 hours, the methylene chloride layer was separated, washed successively with saturated aqueous sodium sulfite solution, saturated aqueous sodium hydrogencarbonate solution and saturated saline solution, dried with magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.38 g of 1-(3-(4-chlorophenylsulfinyl)propyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene (73% yield), n_(D) ²⁴.5 1.5962.

PRODUCTION EXAMPLE 34 Production of Compound (285)

A mixture of 0.50 g of 1-(3-(4-chlorophenylthio)propyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene and 20 ml of methylene chloride was stirred under cooling with ice-water, to which 0.52 g of m-chloroperbenzoic acid was added. After stirring at room temperature for 24 hours, the methylene chloride layer was separated, washed successively with saturated aqueous sodium sulfite solution, saturated aqueous sodium hydrogencarbonate solution and saturated saline solution, dried with magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.44 g of 1-(3-(4-chlorophenylsulfonyl)propyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene (82% yield), n_(D) ²⁴.5 1.5863.

PRODUCTION EXAMPLE 35 Production of Compound (242) by Production Process E

In a reaction vessel were placed 0.53 g of 4-(3-fluorophenyl)-3-buten-1-ol and 50 ml of ethyl acetate, and the air in the vessel was exchanged for nitrogen. Then, 0.1 g of 10% palladium carbon was added thereto, and the nitrogen in the vessel was exchanged for hydrogen, followed by vigorous stirring at room temperature for 24 hours. After the hydrogen in the vessel was exchanged for nitrogen, the reaction solution was filtered through a celite bed, and the filtrate was concentrated. The residue was subjected to silica gel chromatography, which afforded 0.48 g of 4-(3-fluorophenyl)-1-butanol.

To a solution of 0.18 g of 4-(3-fluorophenyl)-1-butanol, 0.30 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran, a solution of 0.20 ml of N,N-diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran was added dropwise, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.38 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-fluorophenyl) butyloxy)benzene (83% yield), n_(D) ²⁵.0 1.5620.

PRODUCTION EXAMPLE 36 Production of Compound (239) by Production Process E

A mixture of 4.0 g of (3-hydroxypropyl)triphenylphosphonium bromide and 20 ml of tetrahydrofuran was cooled to 0° C., to which 12.5 ml of 1.6M n-butyl lithium (as a hexane solution) was slowly added dropwise. The reaction mixture was stirred at 0° C. for 30 minutes, to which a mixture of 1.24 g of 3-fluorobenzaldehyde and 10 ml of tetrahydrofuran was slowly added dropwise at the same temperature, followed by further stirring at room temperature for 6 hours. The reaction mixture was poured into ice-water, acidified by the addition of 10% hydrochloric acid, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.70 g of 4-(3-fluorophenyl)-3-buten-1-ol.

To a solution of 0.17 g of 4-(3-fluorophenyl)-3-buten-1-ol, 0.30 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.20 ml of N,N-diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After the stirring was continued at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.38 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-fluorophenyl)-3-butenyloxy)benzene (84% yield), n_(D) ²⁵.5 1.5857.

PRODUCTION EXAMPLE 37 Production of Compound (270) by Production Process E

To a mixture of 20.4 g of 1,3-dibromopropane, 7.1 g of potassium carbonate and 100 ml of N,N-dimethylformamide was added dropwise a solution of 9 g of 4-trifluoromethoxyphenol dissolved in 30 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was filtered, and the solvent was removed from the filtrate by distillation under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 9.1 g of 1-(3-bromopropyloxy)4-trifluoromethoxybenzene (60% yield).

To a mixture of 0.6 g of 3,5-diethyl-4- 3-(4-(trifluoromethoxy)phenoxy)propyloxy!phenol thus obtained, 0.21 g of potassium carbonate and 10 ml of N,N-dimethylformamide was added dropwise a solution of 0.30 g of 1,1,3-trichloro-1-propene dissolved in 5 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was poured into ice-water, and extracted twice with 100 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.56 g of 3,5-diethyl-4- 3-(4-trifluoromethoxyphenoxy)propyloxyl-1-(3,3-dichloro-2-propenyloxy)benzene (80% yield), n_(D) ²⁵.9 1.5115.

PRODUCTION EXAMPLE 38 Production of Compound (216) by Production Process D

First, 0.35 g of 1-(3-bromopropyloxy)-4-trifluoromethylbenzene (prepared in the same manner as described above for 1-(3-bromopropyloxy)-4-trifluoromethoxybenzene) and 0.2 g of potassium carbonate were dissolved in 100 ml of N,N-dimethylformamide, to which 0.3 g of 2-chloro-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenol was added, and the mixture was stirred at room temperature for 24 hours. The reaction mixture was mixed with 200 ml of diethyl ether, washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.50 g of 3-chloro-4- 3-(4-trifluoromethylphenoxy) propyloxy!-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzene (94% yield), n_(D) ²³.0 1.5330.

Production Example 39 Production of compound (272) by production process A

To a mixture of 0.6 g of 3-ethyl-4- 3-(4-trifluoromethoxyphenoxy)propyloxy!-5-methylphenol, 0.22 g of potassium carbonate and 10 ml of N,N-dimethylformamide was added dropwise a solution of 0.31 g of 1,1,3-trichloro-1-propene dissolved in 5 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was poured into ice-water, and extracted twice with 100 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.5 g of 3-ethyl-4- 3-(4-trifluoromethoxyphenoxy)propyloxy!-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzene (71% yield), n_(D) ²³.5 1.5150.

The following are specific examples of the present compounds under the corresponding compound numbers with their physical properties, if measured.

(1) 3,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.6 1.5067

(2) 3,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)-1-(3,3-dibromo-2-propenyloxy)benzene n_(D) ²⁴.6 1.5333

(3) 2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 75.8° C.

(4) 2,6-Dichloro-4-(3,3-dibromo-2-propenyloxy)-1-(3,3-dibromo -2-propenyloxy)benzene n_(D) ²².5 1.6459

(5) 3,5-Dichloro-4-ethoxy-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.5 1.5561

(6) 3,5-Dichloro-4-ethoxy-1-(3,3-dibromo-2-propenyloxy)benzene n_(D) ²⁴.5 1.5865

(7) 3,5-Dichloro-4-(3,3-dibromo-2-propenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p 51.9° C.

(8) 3,5-Dichloro-4-(4-trifluoromethylbenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 77.1° C.

(9) 3,5-Dichloro-4-(3-methyl-2-butenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5556

(10) 3,5-Dichloro-4-(3-chloro-2-butenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5552

(11) 3,5-Dichloro-4-(3-chloro-2-propenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5694

(12) 3,5-Dichloro-4-(3-trifluoromethylbenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 51.6° C.

(13) 3,5-Dichloro-4-(4-tert-butoxycarbonylbenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 78.3° C.

(14) 3,5-Dichloro-4-(4-tert-butylbenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.5 1.5670

(15) 3,5-Dichloro-4-(4-methoxy benzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 95.4° C.

(16) 3,5-Dichloro-4-(4-cynnamyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 51.3° C.

(17) 3,5-Dichloro-4-(3,5-bis(trifluoromethyl)benzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 58.8° C.

(18) 3,5-Dichloro-4-(3-methoxybenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 73.9° C.

(19) 3,5-Dichloro-4-(2-naphthylmethyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 86.7° C.

(20) 3,5-Dichloro-4-(1-naphthylmethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 84.1° C.

(21) 3,5-Dichloro-4-(3-cyanobenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 122.9° C.

(22) 3,5-Dichloro-4-(3-fluorobenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 75.3° C.

(23) 3,5-Dichloro-4-(3-chlorobenzoyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 87.0° C.

(24) 3,5-Dichloro-4-(3-bromobenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 73.6° C.

(25) 3,5-Dichloro-4-benzyloxy-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 46.8° C.

(26) 3,5-Dichloro-4-(3-methylbenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 43.6° C.

(27) 3,5-Dichloro-4-(3-fluoro-4-phenoxy)benzyl oxy)-1-(3,3-dichloro-2-propenyloxy) benzene n_(D) ²².5 1.5973

(28) 3,5-Dichloro-4-(4-chlorobenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 67.8° C.

(29) 3,5-Dichloro-4-(2-chlorobenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 82.0° C.

(30) 3,5-Dichloro-4-(2,4-dichloro benzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 89.3° C.

(31) 3,5-Dichloro-4-(2,5-dichloro benzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 98.9° C.

(32) 3,5-Dichloro-4-(3,4-dichloro benzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 95.2° C.

(33) 3,5-Dichloro-4-(4-bromobenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 85.5° C.

(34) 3,5-Dichloro -4-(3-phenoxybenzyloxy)-1-(3,3-dichloro -2-propenyloxy)benzene n_(D) ²⁵.5 1.6066

(35) 3,5-Dichloro -4-(4-phenoxy benzyloxy)-1-(3,3-dichloro -2-propenyloxy)benzene n_(D) ²⁵.5 1.6084

(36) 3,5-Dichloro-4-(4-phenylbenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 112.6° C.

(37) 3,5-Dichloro-4-((α-phenethyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁶.0 1.5830.

(38) 3,5-Dichloro-4-(3,4-methylenedioxybenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 97.3° C.

(39) 3,5-Dichloro-4-(3-benzyloxybenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.6040

(40) 3,5-Dichloro-4-(1-(2-methylnaphthyl)methoxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 120.3° C.

(41) 3,5-Dichloro-4-(4-fluoro-3-phenoxy)benzyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene n_(D) ²².5 1.6062

(42) 3,5-Dichloro-4-(β-phenethyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁸.5 1.5816

(43) 3,5-Dichloro-4-(2-methyl-3-phenylbenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁸.5 1.6125

(44) 3,5-Dichloro-4-(2-phenylbenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁸.5 1.6164

(45) 3,5-Dichloro-4-(4-fluorobenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 72.0° C.

(46) 3,5-Dichloro-4-(2-methylbenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 52.9° C.

(47) 4-(2-Chlorobenzyloxy)-3,5-dichloro-1-(3,3-dibromo-2-propenyloxy)benzene m.p. 83.5° C.

(48) 3,5-Dichloro-4-(2-bromobenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 82.5° C.

(49) 3,5-Dichloro-4-(2-fluorobenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 60.6° C.

(50) 3,5-Dichloro-4-(2,6-dichloro benzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 135.6° C.

(51) 3,5-Dichloro-4-(2-bromoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5813

(52) 3,5-Dichloro-4-(2,2-dichloroethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5719

(53) 3,5-Dichloro-4-(4-(methylthio)butoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5673

(54) 3,5-Dichloro-4-(3-phenylpropoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.5794

(55) 3,5-Dichloro-4-(3-isopropoxy-4-chlorobenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².5 1.5780

(56) 3,5-Dichloro-4-(4-benzyloxybenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.6047

(57) 3,5-Dichloro-4-(4-chloro-3-phenoxybenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.6112

(58) 3,5-Dichloro-4-(4-methoxy-3-benzyloxybenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².0 1.5958

(59) 3,5-Dichloro-4-(3-(3,4-dichlorophenoxy)benzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².0 1.6160

(60) 3,5-Dichloro-4-(3-(3-trifluoromethylbenzyloxy)benzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².0 1.5713

(61) 3,5-Dichloro-4-(3-(4-chlorophenoxy)benzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².5 1.6087

(62) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(3-phenoxyphenyl)propoxy)benzene n_(D) ²⁵.0 1.5928

(63) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-chloro phenethyloxy)benzene n_(D) ²⁴.5 1.5868

(64) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-((4-phenyl)butyloxy)benzene n_(D) ²⁶.0 1.5716

(65) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-((5-phenyl)pentyloxy)benzene n_(D) ²⁶.0 1.5690

(66) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(1-indanyloxy)benzene n_(D) ²⁶.0 1.5982

(67) 3,5-Dichloro -1-(3,3-dichloro-2-propenyloxy)-4-(2-methyl-1-(4-phenoxyphenyl)-n-propoxy)benzene n_(D) ²⁶.0 1.5885

(68) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-fluoro-5-(4-fluorophenoxy)benzyloxy)benzene n_(D) ²⁶.0 1.5871

(69) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-fluorophenethyloxy)benzene n_(D) ²⁶.5 1.5711

(70) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-bromophenethyloxy)benzene n_(D) ²⁶.5 1.5985

(71) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-methylphenethyloxy)benzene n_(D) ²⁶.5 1.5815

(72) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-methoxyphenethyloxy)benzene n_(D) ²⁶.5 1.5806

(73) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(1-(4-phenoxyphenyl)ethoxy)benzene n_(D) ²⁵.0 1.6007

(74) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-chloro phenethyloxy)benzene n_(D) ²⁴.5 1.5872

(75) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-(1-naphthyl)ethoxy)benzene n_(D) ²⁴.4 1.6189

(76) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-phenoxyethoxy)benzene n_(D) ²⁵.0 1.5836

(77) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-phenoxypropyloxy)benzene n_(D) ²⁵.0 1.5762

(78) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-bromo-5-phenoxybenzyloxy)benzene n_(D) ²⁶.5 1.6188

(79) 3,5-Dichloro-1-(3,3-dichloro -2-propenyloxy)-4-(4-(4-(trifluoromethyl)phenoxy)benzyloxy)benzene n_(D) ²⁶.5 1.5730

(80) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-tert-butylphenoxy)benzyloxy)benzene n_(D) ²⁶.5 1.5889

(81) 3,5-Dichloro-1-(3,3-dichloro -2-propenyloxy)-4-(6-phenylhexyloxy)benzene n_(D) ²⁶.0 1.5702

(82) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-methylphenoxy)benzyloxy)benzene n_(D) ²⁶.0 1.6019

(83) 3,5-Dichloro-1-(3,3-dichloro -2-propenyloxy)-4-(3-(3,5-dichlorophenoxy)benzyloxy) benzene n_(D) ²⁶.0 1.6148

(84) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-(3-chlorophenyl)ethoxy)benzene n_(D) ²⁶.0 1.5897

(85) 3,5-Dichloro-1-(3,3-dichloro-2-propenoyloxy)-4-(2-(2-(trifluoromethyl)phenyl)ethoxy) benzene n_(D) ²⁶.0 1.5516

(86) 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(2-(3-trifluoromethylphenyl)ethoxy)benzene

(87) 3,5-Dichloro -4-methoxymethoxy-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁶.5 1.5596

(88) 3,5-Dichloro-4-(3-(3-trifluoromethylphenyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5430

(89) 3,5-Dichloro-4-(3-(3-chlorophenyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5828

(90) 3,5-Dichloro-4-(3-(4-chlorophenyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5832

(91) 3,5-Dichloro-4-(3-(4-chlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5822

(92) 3,5-Dichloro-4-(2-(4-chlorophenoxy)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 78.6° C.

(93) 3,5-Dichloro-4-(3-(4-fluorophenoxy)benzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5961

(94) 3,5-Dichloro-4-(4-ethoxybenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 84.0° C.

(95) 3,5-Dichloro -4-(2-(phenylthio)ethoxy)-1-(3,3-dichloro -2-propenyloxy)benzene n_(D) ²⁵.5 1.6063

(96) 3,5-Dichloro-4-(3-trifluoromethoxybenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5416

(97) 3,5-Dichloro-4-(4-trifluoromethoxybenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 72.1° C.

(98) 3,5-Dichloro-4-(3-(3-chlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5817

(99) 3,5-Dichloro-4-(3-(4-bromophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5917

(100) 3,5-Dichloro-4-(3-(4-trifluoromethoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5342

(101) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl benzoate n_(D) ²⁵.0 1.5698

(102) 3,5-Dimethyl-4-benzyloxy-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²¹.0 1.5697

(103) 3,5-Dimethyl-4-benzyloxy-1-(3,3-dibromo-2-propenyloxy)benzene m.p. 70.2° C.

(104) 3-Chloro-5-methyl-4-benzyloxy-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5793

(105) 3-Chloro-5-methyl-4-benzyloxy-1-(3,3-dibromo-2-propenyloxy)benzene n_(D) ²⁵.0 1.5998

(106) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl benzoate n_(D) ²³.5 1.5711

(107) 3,5-Dichloro -4-(3-(4-tert-butylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.8 1.5601

(108) 3,5-Dichloro-4-(3-(4-ethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.8 1.5673

(109) 3,5-Dichloro-4-(3-(3-(trifluoromethyl)phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5443

(110) 3,5-Dichloro-4-(3-(3-fluorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5647

(111) 3,5-Dichloro-4-(3-(4-ethoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5620

(112) 3,5-Dichloro-4-(3-(4-benzylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.3 1.5761

(113) 3,5-Dichloro-4-(3-(4-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5693

(114) 3,5-Dichloro-4-(3-(4-fluorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².3 1.5689

(115) 3,5-Dichloro-4-(3-((4-(trifluoromethoxy)phenyl))phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².3 1.5751

(116) 3,5-Dichloro-4-(3-(3-chloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)-phenoxy)propyloxy) 1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².3 1.5710

(117) 3,5-Dichloro-4-(3-(4-(1,1,3,3-tetramethylbutyl)phenoxy)propyloxy)-1(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².3 1.5570

(118) 3,5-Dichloro-4-(3-(4-n-octyloxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².3 1.5526

(119) 3,5-Dichloro-4-(2-(3-fluorophenyl)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5548

(120) 3,5-Dichloro-4-(2-(3-bromophenyl)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5900

(121) 3,5-Dichloro-4-(3-(3-fluorophenyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².0 1.5730

(122) 3,5-Dichloro-4-(3-(4-fluorophenyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.5669

(123) 3,5-Dichloro-4-(3-(3,4-dichlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.7 1.5837

(124) 3,5-Dichloro-4-(3-(2,3,4-trichlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5857

(125) 3,5-Dichloro-4-(3-(2,4,6-trichlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5799

(126) 3,5-Dichloro-4-(3-(2,3,6-trichlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.7 1.5857

(127) 3,5-Dichloro-4-(3-(2,4,5-trichlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.7 1.5870

(128) 3,5-Dichloro-4-(3-(2,3,4,6-tetrachlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.7 1.5870

(129) 3,5-Dichloro-4-(3-(4-methylthiophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.7 1.5898

(130) 3,5-Dichloro-4-(3-(3-ethoxylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.7 1.5628

(131) 3,5-Dichloro-4-(3-(3-methoxylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.7 1.5625

(132) 2-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl (4-chloro)benzoate m.p. 72.3° C.

(133) 2-(2,6-Dichloro-4-(3,3-dibromo-2-propenyloxy)phenoxy)ethyl (4-chloro)benzoate n_(D) ²⁴.0 1.5811

(134) 2-(2,6-Dichloro-4-(3,3-dibromo-2-propenyloxy)phenoxy)ethyl benzoate n_(D) ²³.5 1.5794

(135) 3,5-Dichloro-4-(3-(3-trifluoromethoxylphenyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5354

(136) 3,5-Dichloro-4-(3-(4-trifluoromethoxylphenyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5337

(137) 2-(2,6-Dichloro-4-(3,3-dibromo-2-propenyloxy)phenoxy)ethyl (4-trifluoromethoxy)benzoate n_(D) ²².5 1.5320

(138) 2-(2,6-Dichloro-4-(3,3-dibromo-2-propenyloxy)phenoxy)ethyl (3,5-dichloro)benzoate m.p. 86.1° C.

(139) 3,5-Dichloro-4-(3-(4-(1,1,2,2-tetrafluoroethoxy)phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.5262

(140) 3,5-Dichloro-4-(3-(4-(1,1,2,2-tetrafluoro-2-bromoethoxy)phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.5302

(141) 3,5-Dichloro-4-(3-(4-bromodifluoromethoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.5481

(142) 3,5-Dichloro-4-(2-(4-trifluoromethylphenyl)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².0 1.5462

(143) 3,5-Dichloro-4-(3-(3-bromophenyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².0 1.5913

(144) 3,5-Dichloro-4-(4-(4-chlorophenyl)-3-butenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 53.6° C.

(145) 3,5-Dichloro -4-(4-(4-fluorophenyl)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².0 1.5653

(146) 3,5-Dichloro-4-(4-(4-trifluoromethylphenyl)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².0 1.5409

(147) 3,5-Dichloro-4-(4-(4-trifluoromethoxyphenyl)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².0 1.5325

(148) 2-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl phenylacetate n_(D) ²¹.5 1.5717

(149) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (2-chloro)benzoate n_(D) ²⁴.0 1.5744

(150) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (3-chloro)benzoate n_(D) ²⁴.0 1.5766

(151) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-chloro)benzoate n_(D) ²⁴.0 1.5791

(152) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-ethoxy)benzoate n_(D) ²⁴.0 1.5715

(153) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-trifluoromethoxy)benzoate n_(D) ²⁴.0 1.5370

(154) 2-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl (2-chloro)benzoate M.p. 51.9° C.

(155) 2-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl (3-chloro)benzoate n_(D) ²⁴.8 1.5793

(156) 3,5-Dichloro-4-(2-(4-chlorophenylthio)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².5 1.6121

(157) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (3-phenoxy)benzoate n_(D) ²⁴.5 1.5753

(158) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-fluoro)benzoate n_(D) ²⁴.5 1.5627

(159) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4bromo)benzoate n_(D) ²⁴.5 1.5832

(160) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (2-fluoro-4-trifluoromethyl)benzoate n_(D) ²⁴.5 1.5351

(161) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (3,5-bistrifluoromethyl)benzoate n_(D) ²⁴.5 1.5146

(162) 3,5-Dichloro-4-(3-(4-isopropoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.4 1.5608

(163) 3,5-Dichloro-4-(3-(3-isopropoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.4 1.5611

(164) 3,5-Dichloro-4-(3-(4-(2,2,2-trifluoroethoxy)phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.4 1.5371

(165) 3,5-Dichloro-4-(3-(3-(2,2,2-trifluoroethoxy)phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.4 1.5361

(166) 3,5-Dichloro-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.4 1.5390

(167) 3,5-Dichloro-4-(3-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.4 1.5267

(168) 3,5-Dichloro-4-(3-(3-(2-bromo-1,1,2,2-tetrafluoroethoxy)phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.4 1.5343

(169) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (2,4-dichloro)benzoate n_(D) ²⁵.0 1.5850

(170) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (3,4-diethoxy)benzoate n_(D) ²⁵.0 1.5664

(171) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (3-trifluoromethyl)benzoate n_(D) ²⁵.0 1.5410

(172) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (3,4-dimethoxy)benzoate m.p. 66.2° C.

(173) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-isopropyl)benzoate

(174) 3,5-Dichloro-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n.sub.D²⁵.0 1.5666

(175) 3,5-Dichloro-4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 115.0° C.

(176) 3,5-Dichloro-4-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 111.0° C.

(177) 3-Chloro-5-methyl4-(2-(4-bromophenyl)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.2 1.5865

(178) 3-Chloro-5-methyl-4-(3-(4-chlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5720

(179) 3-Chloro-5-methyl-4-(4-phenylbutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.5 1.5625

(180) 3-Chloro-5-methyl-4-(2-(4-bromophenyl)ethoxy)-1-(3,3-dibromo-2-propenyloxy)benzene m.p. 70.7° C.

(181) 3,5-Dichloro-4-(3-(phenylthio)propyloxy) 1-(3,3-dibromo-2-propenyloxy)benzene n_(D) ²⁶.0 1.5997

(182) 3,5-Dichloro-4-(3-(4-chlorophenylthio)propyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene n_(D) ²⁶.0 1.6035

(183) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl 1-naphthoate n_(D) ²⁵.5 1.5978

(184) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl 2-naphthoate m.p. 71.4° C.

(185) 3,5-Dichloro-4-(3-(3-trifluoromethoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.4 1.5343

(186) 4-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl (4-ethoxy)benzoate n_(D) ²⁴.0 1.5652

(187) 2-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl (4-isopropoxy)benzoate n_(D) ²⁴.0 1.5703

(188) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-isopropoxy)benzoate n_(D) ²⁴.0 1.5650

(189) 2-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl (4-ethoxy)benzoate m.p. 77.8° C.

(190) 3,5-Dichloro-4-(3,7-dimethyloctyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.7 1.5340

(191) 3,5-Dichloro-4-(3,7-dimethyl -6-octenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.7 1.5446

(192) 3,5-Dichloro(3,7-dimethyl-2,6-octadienoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.7 1.5762

(193) 3,5-Dichloro-4-(n-octyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.5 1.5297

(194) 3,5-Dichloro-4-(2-(4-chlorobenzyloxy)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.7 1.5777

(195) 4-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl (2-chloro)benzoate n_(D) ²³.5 1.5734

(196) 4-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl (3-chloro)benzoate n_(D) ²³.5 1.5732

(197) 4-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl (4-chloro)benzoate n_(D) ²³.5 1.5746

(198) 4-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl (4-trifluoromethoxy)benzoate n_(D) ²³.5 1.5326

(199) 4-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl (4-isopropoxy)benzoate n_(D) ²³.5 1.5622

(200) 3,5-Dichloro-4-(3-(4-trifluoromethylphenylthio)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5635

(201) 3,5-Dichloro-4-(3-(4-tert-butylphenylthio)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5777

(202) 3,5-Dichloro-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5367

(203) 3,5-Dichloro-4-(4-(4-isopropyloxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5578

(204) 3,5-Dibromo-4-(2-(4-bromophenyl)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.6180

(205) 3,5-Dibromo-4-(3-(4-chlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5983

(206) 3,5-Dibromo-4-(4-phenylbutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n.sub.D²³.0 1.5918

(207) 3,5-Dibromo-4-(4-(4-chlorophenyl)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²¹.5 1.5721

(208) 2-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl (3-ethoxy)benzoate n_(D) ²⁴.5 1.5716

(209) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (3-ethoxy)benzoate n_(D) ²⁴.5 1.5646

(210) 4-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl (3-ethoxy)benzoate n_(D) ²⁴.5 1.5585

(211) 2-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl (4-trifluoromethyl)benzoate n_(D) ²⁵.5 1.5427

(212) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-trifluoromethyl)benzoate n_(D) ²⁵.5 1.5396

(213) 3,5-Dichloro-4-(3-methyl-3-(4-chlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.5693

(214) 3,5-Dichloro-4-(1-methyl-3-(4-chlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.5613

(215) 3,5-Dichloro-4-(3-methyl-3-butenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(216) 3-Chloro -5-methyl-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5330

(217) 3,5-Dichloro-4-(3-(4-methoxyphenylthio)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5990

(218) 3,5-Dichloro-4-(3-(4-fluorophenylthio)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5844

(219) 3,5-Dichloro-4-(3-(2,3,5,6-tetrafluorophenylthio)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5619

(220) 3,5-Dichloro-4-(3-(3-chlorophenylthio)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.6004

(221) 3,5-Dichloro-4-(3-(4-bromophenylthio)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.6117

(222) 3,5-Dichloro-4-(4-(4-chlorophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 54.5° C.

(223) 3,5-Dichloro-4-(4-(3-isopropoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.3 1.5615

(224) 3,5-Dichloro-4-(4-(3-trifluoromethoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.3 1.5355

(225) 3,5-Dichloro-4-(4-(4-(1,1,2,2-tetrafluoroethoxy)phenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.3 1.5283

(226) 3,5-Dichloro-4-(4-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.3 1.5298

(227) 3,5-Dichloro-4-(4-(4-(2,2,2-trifluoroethoxy)phenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.3 1.5384

(228) 3,5-Dichoro-4-(4-(3-(2,2,2-trifluoroethoxy)phenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.3 1.5431

(229) 3,5-Dichloro-4-(4-(4-difluoromethoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.3 1.5484

(230) 3,5-Dichloro-4-(4-(3-difluoromethoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.3 1.5446

(231) 3,5-Dichloro-4-(3-(4-difluoromethoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.3 1.5519

(232) 3,5-Dichloro-4-(3-(3-difluoromethoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.3 1.5500

(233) 3,5-Dichloro-4-(4-(4-trifluoromethylphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.3 1.5418

(234) 3,5-Dichloro-4-(4-(3-trifluoromethylphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.3 1.5375

(235) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-chloro)phenylacetate n_(D) ²².0 1.5698

(236) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-chloro)cinnamate m.p. 62.2° C.

(237) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-chloro)phenoxyacetate n_(D) ²².0 1.5709

(238) 3,5-Dichloro-4-(3-(N-methylanilino)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5887

(239) 3,5-Dichloro-4-(4-(3-fluorophenyl)-3-butenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5857

(240) 3,5-Dichloro-4-(4-(3-trifluoromethylphenyl)-3-butenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5588

(241) 3,5-Dichloro-4-(4-(3-trifluoromethoxyphenyl)-3-butenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5502

(242) 3,5-Dichloro -4-(4-(3-fluorophenyl)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5620

(243) 3,5-Dichloro-4-(4-(3-trifluoromethylphenyl)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5373

(244) 3,5-Dichloro-4-(4-(3-trifluoromethoxyphenyl)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5314

(245) 2-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl (4-(2,2,2-trifluoroethoxy)benzoate m.p. 57.6° C.

(246) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-(2,2,2-trifluoroethoxy)benzoate m.p. 53.9° C.

(247) 3,5-Dichloro-4-((3-ethoxycarbonyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².0 1.5367

(248) 3,5-Dichloro-4-(3-(4-(trifluoromethoxy)phenoxycarbonyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5307

(249) 3,5-Dichloro -4-(2-methyl-3-(4-chlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(250) 3-Chloro-5-methyl-4-(3-(4-trifluoromethoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5279

(251) 3-(2-Chloro-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-bromo)benzoate n_(D) ²⁴.0 1.5798

(252) 3,5-Dichloro-4-(2-(4-isopropoxyphenyl)ethoxy)-1-(3,3-dichloro -2-propenyloxy)benzene n_(D) ²⁵.0 1.5632

(253) 3,5-Dichloro-4-(2-(4-(trifluoromethoxy)phenyl)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5370

(254) 3,5-Dichloro-4-(3-(4-bromophenyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5891

(255) 3,5-Dichloro-4-(3-(4-(trifluoromethyl)phenyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5367

(256) 3,5-Dimethyl-4-(3-(4-chlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5638

(257) 3,5-Dichloro-4-(4-(4-chlorophenoxy)-2-(Z)-butenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²¹.9 1.5827

(258) 3,5-Dichloro-4-(4-(4-chlorophenoxy)-2-(E)-butenyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²¹.9 1.5824

(259) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-difluoromethyl)benzoate n_(D) ²³.0 1.5535

(260) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-(1,1,2,2-tetrafluoroethoxy))benzoate n_(D) ²³.0 1.5329

(261) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (3-methyl-2-(4-chlorophenyl))butyrate n_(D) ²³.0 1.5565

(262) 3,5-Dichloro-4-(4-(4-chlorophenylthio)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².5 1.5910

(263) 3,5-Dichloro -4-(4-(4-trifluoromethylphenylthio)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².5 1.5608

(264) 3,5-Dichloro-4-(4-(4-hydroxyphenylthio)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².5 1.5998

(265) 3,5-Dimethyl-4-(3-(4-trifluoromethoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².0 1.5183

(266) 3,5-Dichloro-4-(4-(4-methoxyphenylthio)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5831

(267) 3,5-Dichloro-4-(4-(4-isopropoxyphenylthio)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5718

(268) 3,5-Dichloro-4-(3-(4-chlorophenylsulfenyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.5 1.5962

(269) 3,5-Diisopropyl -4-(4-(4-trifluoromethoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5070

(270) 3,5-Diethyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.9 1.5115

(271) 3,5-Diethyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)-1-(3,3-bromo-2-propenyloxy)benzene n_(D) ²⁵.9 1.5292

(272) 3-Ethyl-5-methyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene n_(D) ²³.5 1.5150

(273) 3-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl (4-trifluoromethyl)cinnamate n_(D) ²⁵.5 1.5542

(274) 3,5-Dichloro-4-(3-(4-trifluoromethoxyanilino)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5503

(275) 3,5-Dichloro-4-(3-anilino)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.0 1.5974

(276) 3,5-Dichloro-4-(3-(4-trifluoromethoxyanilino)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.5617

(277) 3,5-Dichloro-4-(3-(N-methyl-4-trifluoromethylanilino)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5593

(278) 3,5-Dichloro-4-(3-(N-acetyl-4-trifluoromethylanilino) propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.5 1.5395

(279) 3,5-Dichloro-4-(3-(4-trifluoromethoxyphenylthio)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.5569

(280) 3,5-Dichloro-4-(4-trifluoromethylbenzyloxy)-1-(3,3-dichloro-2-propenylthio)benzene

(281) 3,5-Dichloro-4-(2-(4-trifluoromethylphenyl)ethoxy-1-(3,3-dichloro-2-propenyloxy) benzene

(282) 3,5-Dichloro -4-(3-(4-trifluoromethylphenyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁵.0 1.5367

(283) 3,5-Dichloro-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 52.1° C.

(284) 3-Ethyl-5-methyl-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²¹.5 1.5234

(285) 3,5-Dichloro-4-(3-(4-chlorophenylsulfonyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.5 1.5863

(286) 2,3,5,6-Tetrachloro-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenylthio)benzene

(287) 2,3,5,6-Tetrachloro-1,4-bis(3,3-dichloro-2-propenyloxy)benzene

(288) 3,5-Dichloro-4-(4-anilino)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²¹.5 1.5919

(289) 3,5-Dichloro-4-(4-(4-trifluoromethylanilino)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²¹.5 1.5606

(290) 3,5-Dichoro-4-(4-(4-trifluoromethoxyanilino)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²¹.5 1.5491

(291) 3,5-Diethyl-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁰.0 1.5230

(292) 3,5-Dichloro-4-(3-(4-isopropoxycarbonylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².7 1.5440

(293) 3,5-Dichloro-4-(3-(4-methoxycarbonylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².7 1.5519

(294) 3-Chloro-5-methyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5208

(295) 3-Chloro-5-methyl-4-(4-(4-trifluoromethylphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5285

(296) 3-Chloro-5-methyl-4-(4-(4-chlorophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 54.5° C.

(297) 3-Chloro-5-methyl-4-(3-(4-bromophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5812

(298) 3-Chloro-5-methyl-4-(4-(4-bromophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 51.6° C.

(299) 3-Chloro-5-methyl-4-(3-(4-isopropoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5485

(300) 3-Chloro-5-methyl-4-(4-(4-isopropoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²⁴.0 1.5482

(301) 3-Ethyl-5-methyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5150

(302) 3-Ethyl-5-methyl-4-(4-(4-trifluoromethylphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.0 1.5221

(303) 3-Ethyl-5-methyl-4-(3-(4-chlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.5562

(304) 3-Ethyl-5-methyl-4-(4-(4-chlorophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²¹.3 1.5554

(305) 3-Ethyl-5-methyl-4-(3-(4-bromophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.5670

(306) 3-Ethyl-5-methyl-4-(4-(4-bromophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²¹.3 1.5620

(307) 3-Ethyl-5-methyl-4-(3-(4-isopropoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²³.5 1.5430

(308) 3-Ethyl -5-methyl-4-(4-(4-isopropoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²¹.3 1.5429

(309) 3,5-Diethyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(310) 3,5-Diethyl-4-(4-(4-trifluoromethylphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(311) 3,5-Diethyl-4-(3-(4-chlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(312) 3,5-Diethyl-4-(4-(4-chlorophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(313) 3,5-Diethyl-4-(3-(4-bromophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(314) 3,5-Diethyl-4-(4-(4-bromophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(315) 3,5-Diethyl-4-(3-(4-isopropoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(316) 3,5-Diethyl-4-(4-(4-isopropoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(317) 3,5-Diisopropyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(318) 3,5-Diisopropyl-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(319) 3,5-Diisopropyl-4-(4-(4-trifluoromethylphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(320) 3,5-Diisopropyl-4-(3-(4-chlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(321) 3,5-Diisopropyl-4-(4-(4-chlorophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(322) 3,5-Diisopropyl-4-(3-(4-bromophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(323) 3,5-Diisopropyl-4-(4-(4-bromophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(324) 3,5-Diisopropyl-4-(3-(4-isopropoxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

(325) 3,5-Diisopropyl-1-4-(4-(4-isopropoxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

The following are production examples for the intermediate compounds of the general formula IV!, V! or VI!.

Intermediate Production Example 1 Production of Intermediate Compound 1)

A reaction vessel was charged with 25.5 g of hydroquinone monobenzyl ether, 17.9 g of benzoyl chloride, 0.50 g of tetrabutylammonium bromide and 100 ml of toluene, to which 78.6 g of 10% potassium hydroxide solution was slowly added dropwise, while stirring under ice cooling. After 24 hours, the reaction mixture was made weakly acidic by the addition of 20% hydrochloric acid, and the deposited crystals were collected by filtration. The crystals thus obtained were successively washed with 10% hydrochloric acid and water, and dried, which afforded 38 g of 4-benzyloxyphenyl benzoate (98% yield).

A reaction vessel was charged with 38 g of 4-benzyloxyphenyl benzoate and 500 ml of ethanol, and the air in the vessel was replaced with nitrogen. Then, 1.0 g of 10% palladium carbon was added thereto, and the nitrogen in the vessel was replaced with hydrogen, followed by vigorous stirring at room temperature for 24 hours. The hydrogen in the vessel was replaced with nitrogen, after which the reaction mixture was filtered though celite, and the filtrate was concentrated, which afforded 24.5 g of 4-hydroxyphenyl benzoate (94% yield).

A reaction vessel was charged with 24.5 g of 4-hydroxyphenyl benzoate and 500 ml of carbon tetrachloride, to which a solution of 24.8 g of t-butyl hypochlorite dissolved in 20 ml of carbon tetrachloride was slowly added dropwise, while stirring under ice cooling. After 24 hours, the reaction mixture was poured into water, followed by phase separation. The organic layer (i.e., carbon tetrachloride layer) was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 29.5 g of 3,5-dichloro-4-hydroxyphenyl benzoate (91% yield).

A reaction vessel was charged with 1.54 g of 3,5-dichloro-4-hydroxyphenyl benzoate, 0.83 g of potassium carbonate, 1.53 g of 4-fluoro-3-phenoxybenzyl bromide, and 10 ml of N,N-dimethylformamide, followed by stirring at room temperature for 5 hours. The reaction mixture was poured into water, and extracted twice with 50 m of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 2.32 g of 3,5-dichloro-4-(4-fluoro-3-phenoxybenzyloxy)phenyl benzoate (88% yield).

A reaction vessel was charged with 1.36 g of 3,5-dichloro-4-(4-fluoro-3-phenoxybenzyloxy)phenyl benzoate and 10 ml of methanol, to which 4.2 g of 10% potassium hydroxide solution was slowly added dropwise under ice cooling. After stirring for 1 hour, the reaction mixture was made weakly acidic by the addition of 10% hydrochloric acid, and extracted twice with 50 ml of diethyl ether under salting out. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.97 g of 3,5-dichloro-4-(4-fluoro-3-phenoxybenzyloxy)phenol (91% yield), m.p. 144.8° C.

Intermediate Production Example 2 Production of Intermediate Compound 2)

A mixture of 2.27 g of 4-benzoyloxy-2,6-dichlorophenol, 1.29 g of 2-chlorobenzyl chloride, 1.21 g of potassium carbonate and 50 ml of N,N-dimethylformamide was stirred at 80° C. for 6 hours. The reaction mixture was cooled to room temperature, poured in ice water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, and dried with anhydrous magnesium sulfate, followed by removal of the solvent by distillation under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 2.87 g of 1-benzoyloxy-4-(2-chlorobenzyloxy)-3,5-dichlorobenzene (88% yield).

To a mixture of 2.87 g of 1-benzoyloxy-4-(2-chlorobenzyloxy)-3,5-dichlorobenzene and 100 ml of methanol was added dropwise 5.1 g of 10% (w/w) aqueous potassium hydroxide solution, while stirring at room temperature. After stirring at room temperature for 6 hours, the reaction mixture was made weakly acidic by the addition of 10% hydrochloric acid, and the methanol was removed by distillation under reduced pressure. The residue was extracted twice with 100 ml of ethyl acetate. The combined ether layer was washed with water, and dried with anhydrous magnesium sulfate, followed by removal of the solvent by distillation under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 1.17 g of 4-(2-chlorobenzyloxy)-3,5-dichlorophenol (55% yield), m.p. 108.3° C.

Intermediate Production Example 3 Production of Intermediate Compound 264)

A mixture of 27 g of 2-ethyl-6-methylaniline, 36 ml of concentrated sulfuric acid and 100 ml of water was stirred at a temperature of 0°-5° C., to which a solution of 16.1 g of sodium nitrite dissolved in 50 ml of water was added dropwise. Then, 150 g of cold water, 1.5 g of urea and 150 g of ice were added thereto.

This aqueous solution was added dropwise to a mixture of 100 ml of sulfuric acid, 100 ml of water and 150 g of sodium sulfate, while heating to 135° C. under stirring. At the same time, the mixture was subjected to steam distillation. After completion of the addition, an aqueous solution obtained by the steam distillation was subjected to salting out with sodium chloride, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 16 g of 2-ethyl-6-methylphenol (59% yield).

Then, 16 g of 2-ethyl-6-methylphenol was dissolved in 200 ml of chloroform, followed by stirring at 0° C., to which 56.6 g of tetrabutylammonium tribromide was added in small portions. After stirring at room temperature for 1 hour, the solvent was removed by distillation under reduced pressure, and the residue was dissolved in 300 ml of diethyl ether. The solution was successively washed with 10% hydrochloric acid and water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 23 g of 4-bromo-2-ethyl-6-methylphenol (92% yield).

To a mixture of 10 g of 4-bromo-2-ethyl-6-methylphenol, 14.0 g of 1-(3-bromopropyloxy)-4-trifluoromethoxybenzene and 100 ml of N,N-dimethylformamide was added 7 g of potassium carbonate, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was poured into ice water, and extracted twice with 200 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 18.1 g of 4-bromo-2-ethyl-6-methyl-1- 3-(4-trifluoromethoxyphenoxy)propyloxy!benzene 90% yield).

Then, 6.6 g of 4-bromo-2-ethyl-6-methyl-1- 3-(4-trifluoromethoxyphenoxy)propyloxy!benzene was dissolved in 200 ml of tetrahydrofuran, and the solution was stirred at -70° C., to which 9.6 ml of n-butyl lithium solution (in hexane, 1.58 mol/liter) was added dropwise, followed by further stirring at -70° C. for 2 hours. To this reaction mixture was added dropwise a solution of 2.2 g of triethoxy borane dissolved in 60 ml of tetrahydrofuran. Then, the reaction mixture was stirred for 1 hour, while warming to room temperature, and 13 ml of 10% aqueous hydrochloric acid solution was added in small portions, followed by stirring at room temperature for 20 minutes. The tetrahydrofuran layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated, to which 50 ml of toluene was added, and the mixture was heated at 70° C. under stirring, to which 6 ml of 30% aqueous hydrogen peroxide solution was added dropwise. The mixture was heated under reflux for 1 hour, and washed once with water, twice with 10% aqueous ammonium ferrous sulfate solution, and once with water. The toluene layer was dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 3.4 g of 3-ethyl-4- 3-(4-trifluoromethoxyphenoxy)propyloxy!-5-methylphenol (61% yield), n_(D) ²⁵.4 1.4955.

Intermediate Production Example 4 Production of Intermediate Compound 263)

To a mixture of 10 g of 4-bromo-2,6-diethylphenol, 13.5 g of l-(3-bromopropyloxy)-4-trifluoromethoxybenzene and 100 ml of N,N-dimethylformamide was added 6.6 g of potassium carbonate, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was poured into ice water, and extracted twice with 200 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 14.8 g of 4-bromo-2-ethyl-6-methyl-1- 3-(4-trifluoromethoxyphenoxy)propyloxy!benzene (76% yield).

Then, 7.0 g of 4-bromo-2-ethyl-6-methyl-1- 3-(4-trifluoromethoxyphenoxy)propyloxy!benzene was dissolved in 200 ml of tetrahydrofuran, followed by stirring at -70° C., to which 10.0 ml of n-butyl lithium solution (in hexane, 1.58 mol/liter) was added dropwise, followed by further stirring at -70° C. for 2 hours. To this reaction mixture was added dropwise a solution of 2.4 g of trimethoxy borane dissolved in 60 ml of tetrahydrofuran. The reaction mixture was stirred for 1 hour, while warming to room temperature, and 13 ml of 10% aqueous hydrochloric acid solution was added in small portions, followed by stirring at room temperature for 20 minutes. The tetrahydrofuran layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated, to which 50 ml of toluene was added, and the mixture was heated at 70° C. under stirring, to which 6 ml of 30% aqueous hydrogen peroxide solution was added dropwise. The mixture was heated under reflux for 1 hours, and washed once with water, and twice with 10% aqueous ammonium ferrous sulfate solution and once with water. The toluene layer was dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 4.3 g of 3,5-diethyl-4- 3-(4-trifluoromethoxyphenoxy)propyloxy!phenol (50% yield), n_(D) ²⁵.4 1.5060.

The following are specific examples of the intermediate compounds of the general formula IV!, V! or VI! under the corresponding compound numbers with their physical properties, if measured.

1) 3,5-Dichloro-4-(4-fluoro-3-phenoxybenzyloxy)phenol m.p. 144.8° C.

2) 4-(2-Chlorobenzyloxy)-3,5-dichlorophenol m.p. 108.3° C.

3) 3,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenol

4) 3,5-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenol

5) 3,5-Dichloro-4-(3,3-dibromo-2-propenyloxy)phenol

6) 3,5-Dichloro-4-ethoxyphenol

7) 3,5-Dichloro-4-(4-trifluoromethylbenzyloxy)phenol

8) 3,5-Dichloro-4-(3-methyl-2-butenyloxy)phenol

9) 3,5-Dichloro-4-(3-chloro-2-butenyloxy)phenol

10) 3,5-Dichloro-4-(3-chloro-2-propenyloxy)phenol

11) 3,5-Dichloro-4-(4-tert-butoxycarbonylbenzyloxy)phenol

12) 3,5-Dichloro-4-benzyloxyphenol

13) 3,5-Dichloro-4-(3-methylbenzyloxy)phenol

14) 3,5-Dichloro-4-(4-chlorobenzyloxy)phenol

15) 3,5-Dichloro-4-(2,4-dichlorobenzyloxy)phenol

16) 3,5-Dichloro-4-(2,5-dichlorobenzyloxy)phenol

17) 3,5-Dichloro-4-(3,4-dichlorobenzyloxy)phenol

18) 3,5-Dichloro-4-(4-bromobenzyloxy)phenol

19) 3,5-Dichloro-4-(3-phenoxybenzyloxy)phenol

20) 3,5-Dichloro-4-(4-phenoxybenzyloxy)phenol

21) 3,5-Dichloro-4-(4-phenylbenzyloxy)phenol

22) 3,5-Dichloro-4-(α-methylbenzyloxy)phenol

23) 3,5-Dichloro-4-(4-tert-butylbenzyloxy)phenol

24) 3,5-Dichloro-4-(4-methoxybenzyloxy)phenol

25) 3,5-Dichloro-4-(3-phenyl-2-propenyloxy)phenol

26) 3,5-Dichloro-4-(3,5-bis(trifluoromethyl)benzyloxy)phenol

27) 3,5-Dichloro-4-(3-methoxybenzyloxy)phenol

28) 3,5-Dichloro-4-(2-naphthylmethoxy)phenol

29) 3,5-Dichloro-4-(1-naphthylmethoxy)phenol

30) 3,5-Dichloro-4-(3-cyanobenzyloxy)phenol

31) 3,5-Dichloro-4-(3-fluorobenzyloxy)phenol

32) 3,5-Dichloro-4-(3-chlorobenzyloxy)phenol

33) 3,5-Dichloro-4-(3-bromobenzyloxy)phenol

34) 3,5-Dichloro-4-(3,4-methylenedioxybenzyloxy)phenol

35) 3,5-Dichloro-4-(3-benzyloxybenzyloxy)phenol

36) 3,5-Dichloro-4-(1-(2-methylnaphthyl))methoxyphenol

37) 3,5-Dichoro-4-(phenethyloxy)phenol

38) 3,5-Dichloro-4-(2-methyl-3-phenylbenzyloxy)phenol

39) 3,5-Dichloro-4-(2-phenylbenzyloxy)phenol

40) 3,5-Dichloro-4-(4-fluorobenzyloxy)phenol

41) 3,5-Dichloro-4-(2-methylbenzyloxy)phenol

42) 3,5-Dichloro-4-(2-bromobenzyloxy)phenol

43) 3,5-Dichloro-4-(2-fluorobenzyloxy)phenol

44) 3,5-Dichloro-4-(2,6-dichlorobenzyloxy)phenol

45) 3,5-Dichloro-4-(2-bromoethoxy)phenol

46) 3,5-Dichloro-4-(2,2-dichloroethoxy)phenol

47) 3,5-Dichloro-4-(4-(methylthio)butoxy)phenol

48) 3,5-Dichloro-4-(3-phenylpropoxy)phenol

49) 3,5-Dichloro-4-(4-chloro-3-isopropoxybenzyloxy)phenol

50) 3,5-Dichloro-4-(4-benzyloxy)benzyloxyphenol

51) 3,5-Dichloro-4-(4-chloro-3-phenoxy)benzyloxyphenol

52) 3,5-Dichloro-4-(4-methoxy-3-benzyloxy)benzyloxyphenol

53) 3,5-Dichloro-4-(3-(3,4-dichlorophenoxy)benzyloxy)phenol

54) 3,5-Dichloro-4-(3-(3-trifluoromethylbenzyloxy)benzyloxy)phenol

55) 3,5-Dichloro-4-(3-(4-chlorophenoxy)benzyloxy)phenol

56) 3,5-Dichloro-4-(3-trifluoromethylbenzyloxy)phenol

57) 3,5-Dichloro-4-(3-(3-phenoxyphenyl)propyloxy)phenol

58) 3,5-Dichloro-4-(2-(4-chlorophenyl)ethoxy)phenol

59) 3,5-Dichloro-4-(4-phenylbutoxy)phenol

60) 3,5-Dichloro-4-(5-phenylpentyloxy)phenol

61) 3,5-Dichloro-4-(1-indanyloxy)phenol

62) 3,5-Dichloro-4-(2-methyl-1-(4-phenoxyphenyl)propyloxy)phenol

63) 3,5-Dichloro-4-(2-fluoro-5-(4-fluorophenoxy)benzyloxy)phenol

64) 3,5-Dichloro-4-(2-(4-fluorophenyl)ethoxy)phenol

65) 3,5-Dichloro-4-(2-(4-bromophenyl)ethoxy)phenol

66) 3,5-Dichloro-4-(2-(4-methylphenyl)ethoxy)phenol

67) 3,5-Dichloro-4-(2-(4-methoxyphenyl)ethoxy)phenol

68) 3,5-Dichloro-4-(2-(4-phenoxyphenyl)ethoxy)phenol

69) 3,5-Dichloro-4-(2-(2-chlorophenyl)ethoxy)phenol

70) 3,5-Dichloro-4-(2-(2-naphthyl)ethoxy)phenol

71) 3,5-Dichloro-4-(2-phenoxyethoxy)phenol

72) 3,5-Dichloro-4-(3-phenoxyethoxy)phenol

73) 3,5-Dichloro-4-(2-bromo-5-phenoxybenzyloxy)phenol

74) 3,5-Dichloro-4-(4-(4-trifluoromethylphenoxy)benzyloxy)phenol

75) 3,5-Dichloro-4-(3-(4-tert-butylphenoxy)benzyloxy)phenol

76) 3,5-Dichloro-4-(6-phenylhexyloxy)phenol

77) 3,5-Dichloro-4-(3-(4-methylphenoxy)benzyloxy)phenol

78) 3,5-Dichloro-4-(3-(3,5-dichlorophenoxy)benzyloxy)phenol

79) 3,5-Dichloro-4-(2-(3-chlorophenyl)ethoxy)phenol

80) 3,5-Dichloro-4-(2-(2-trifluoromethylphenyl)ethoxy)phenol

81) 3,5-Dichloro-4-(2-(3-trifluoromethylphenyl)ethoxy)phenol

82) 3,5-Dichloro-4-methoxymethoxyphenol

83) 3,5-Dichloro-4-(3-(3-trifluoromethylphenyl)propyloxy)phenol

84) 3,5-Dichloro-4-(3-(3-chlorophenyl)propyloxy)phenol

85) 3,5-Dichloro-4-(3-(4-chlorophenyl)propyloxy)phenol

86) 3,5-Dichloro-4-(3-(4-chlorophenoxy)propyloxy)phenol n_(D) ²⁶.0 1.5525

87) 3,5-Dichloro-4-(2-(4-chlorophenoxy)ethoxy)phenol

88) 3,5-Dichloro-4-(3-(4-fluorophenoxy)benzyloxy)phenol

89) 3,5-Dichloro-4-(4-ethoxybenzyloxy)phenol

90) 3,5-Dichloro-4-(2-phenylthioethoxy)phenol

91) 3,5-Dichloro-4-(3-trifluoromethoxybenzyloxy)phenol

92) 3,5-Dichloro-4-(4-trifluoromethoxybenzyloxy)phenol

93) 3,5-Dichloro-4-(3-(3-chlorophenoxy)propyloxy)phenol

94) 3,5-Dichloro-4-(3-(4-bromophenoxy)propyloxy)phenol

95) 3,5-Dichloro-4-(3-(4-trifluoromethoxyphenoxy)propyloxy)phenol n_(D) ²⁵.0 1.5000

96) 3-(2,6-Dichloro-4-hydroxyphenoxy)propylbenzoate

97) 3,5-Dimethyl-4-benzyloxyphenol m.p. 81.6° C.

98) 3-Chloro-5-methyl-4-benzyloxyphenol n_(D) ²⁵.0 1.5842

99) 4-(2,6-Dichloro-4-hydroxyphenoxy)butylbenzoate

100) 3,5-Dichloro-4-(3-(4-tert-butylphenoxy)propyloxy)phenol

101) 3,5-Dichloro-4-(3-(4-ethylphenoxy)propyloxy)phenol

102) 3,5-Dichloro-4-(3-(3-trifluoromethyl)phenoxy)propyloxy)phenol

103) 3,5-Dichloro-4-(3-(3-trifluoromethoxyphenoxy)propyloxy)phenol

104) 3,5-Dichloro-4-(3-(4-ethoxyphenoxy)propyloxy)phenol

105) 3,5-Dichloro-4-(3-(4-benzylphenoxy)propyloxy)phenol

106) 3,5-Dichloro-4-(3-bromopropyloxy)phenol

107) 3,5-Dichloro-4-(3-(4-fluorophenoxy)propyloxy)phenol

108) 3,5-Dichloro-4-(3-(4-(4-trifluoromethoxyphenyl)phenoxy)propyloxy)phenol

109) 3,5-Dichloro-4-(3-(3-chloro-4-(3-chloro-5-trifluoro methyl-2-pyridyloxy) phenoxy)propyloxy)phenol

110) 3,5-Dichloro-4-(3-(4-(1,1,3,3-tetramethylbutyl)phenoxy)propyloxy)phenol

111) 3,5-Dichloro-4-(3-(4-n-octyloxyphenoxy)propyloxy)phenol

112) 3,5-Dichloro-4-(2-(3-fluorophenyl)ethoxy)phenol

113) 3,5-Dichloro-4-(2-(3-bromophenyl)ethoxy)phenol

114) 3,5-Dichloro-4-(3-(3-fluorophenyl)propyloxy)phenol

115) 3,5-Dichloro-4-(3-(4-fluorophenyl)propyloxy)phenol

116) 3,5-Dichloro-4-(3-(3,4-dichlorophenoxy)propyloxy)phenol

117) 3,5-Dichloro-4-(3-(2,3,4-trichlorophenoxy)propyloxy)phenol

118) 3,5-Dichloro-4-(3-(2,4,6-trichlorophenoxy)propyloxy)phenol

119) 3,5-Dichloro-4-(3-(2,3,6-trichlorophenoxy)propyloxy)phenol

120) 3,5-Dichloro-4-(3-(2,4,5-trichlorophenoxy)propyloxy)phenol

121) 3,5-Dichloro-4-(3-(2,3,4,6-tetrachlorophenoxy)propyloxy)phenol

122) 3,5-Dichloro-4-(3-(4-methylthiophenoxy)propyloxy)phenol

123) 3,5-Dichloro-4-(3-(3-ethoxyphenoxy)propyloxy)phenol

124) 3,5-Dichloro-4-(3-(3-methoxyphenoxy)propyloxy)phenol

125) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl (4-chloro)benzoate

126) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl (4-bromo)benzoate

127) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl benzoate

128) 3,5-Dichloro-4-(3-(3-trifluoromethoxyphenyl)propyloxy)phenol

129) 3,5-Dichloro-4-(3-(4-trifluoromethoxyphenyl)propyloxy)phenol

130) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl (4-trifluoromethoxy)benzoate

131) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl (3,5-dichloro)benzoate

132) 3,5-Dichloro-4-(3-(4-(1,1,2,2-tetrafluoroethoxy)phenoxy)propyloxy)phenol

133) 3,5-Dichloro-4-(3-(4-(1,1,2,2-tetrafluoro-2-bromoethoxy)phenoxy)propyloxy)phenol

134) 3,5-Dichloro-4-(3-(4-bromodifluoromethoxyphenoxy) propyloxy)phenol

135) 3,5-Dichloro-4-(2-(4-trifluoromethylphenyl)ethoxy)phenol

136) 3,5-Dichloro-4-(3-(3-bromophenyl)propyloxy)phenol

137) 3,5-Dichloro-4-(4-(4-chlorophenyl)-3-butenyloxy)phenol

138) 3,5-Dichloro-4-(4-(4-fluorophenyl)butyloxy)phenol

139) 3,5-Dichloro-4-(4-(4-trifluoromethylphenyl)propyloxy)phenol

140) 3,5-Dichloro-4-(4-(4-trifluoromethoxyphenyl)propyloxy)phenol

141) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl phenylacetate

142) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (2-chloro)benzoate

143) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (3-chloro)benzoate

144) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-chloro)benzoate

145) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-ethoxy)benzoate

146) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-trifluoromethoxy)benzoate

147) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl (2-chloro)benzoate

148) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl (3-chloro)benzoate

149) 3,5-Dichloro-4-(2-(4-chlorophenylthio)ethoxy)phenol

150) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (3-phenoxy)benzoate

151) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-fluoro)benzoate

152) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-bromo)benzoate

153) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (2-fluoro-4-trifluoromethyl)benzoate

154) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (3,5-bistrifluoromethyl)benzoate

155) 3,5-Dichloro-4-(3-(4-isopropoxyphenoxy)propyloxy)phenol

156) 3,5-Dichloro-4-(3-(3-isopropoxyphenoxy)propyloxy)phenol

157) 3,5-Dichloro-4-(3-(4-(2,2,2-trifluoroethoxy)phenoxy)propyloxy)phenol

158) 3,5-Dichloro-4-(3-(3-(2,2,2-trifluoroethoxy)phenoxy)propyloxy)phenol

159) 3,5-Dichloro-4-(3-(4-trifluoromethylphenoxy)propyloxy)phenol n_(D) ²⁵.0 1.5151

160) 3,5-Dichloro-4-(3-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)propyloxy)phenol

161) 3,5-Dichloro-4-(3-(3-(2-bromo -1,1,2,2-tetrafluoroethoxy)phenoxy)propyloxy)phenol

162) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (2,4-dichloro)benzoate

163) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (3,4-dichloro)benzoate

164) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (3-trifluoromethyl)benzoate

165) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (3,4-dimethoxy)benzoate

166) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-isopropyl)benzoate

167) 3,5-Dichloro-4-(4-bromobutyloxy)phenol

168) 3,5-Dichloro-4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)phenol

169) 3,5-Dichloro-4-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butoxy)phenol

170) 3-Chloro-5-methyl-4-(2-(4-bromophenyl)ethoxy)phenol

171) 3-Chloro-5-methyl-4-(3-(4-chlorophenoxy)propyloxy)phenol

172) 3-Chloro-5-methyl-4-(4-phenylbutyloxy)phenol

173) 3-Chloro-5-methyl-4-(2-(4-bromophenyl)ethoxy)phenol

174) 3,5-Dichloro-4-(3-(phenylthio)propyloxy)phenol

175) 3,5-Dichloro-4-(3-(4-chlorophenylthio)propyloxy)phenol

176) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl 1-naphthoate

177) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl 2-naphthoate

178) 3,5-Dichloro-4-(3-(3-trifluoromethoxyphenoxy)propyloxy)phenol

179) 4-(2,6-Dichloro-4-hydroxyphenoxy)butyl (4-ethoxy)benzoate

180) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl (4-isopropoxy)benzoate

181) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-isopropoxy)benzoate

182) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl (4-ethoxy)benzoate

183) 3,5-Dichloro-4-(3,7-dimethyloctyloxy)phenol

184) 3,5-Dichloro-4-(3,7-dimethyl-6-octenyloxy)phenol

185) 3,5-Dichloro-4-(3,7-dimethyl-2,6-octadien-1-yl-oxy)phenol

186) 3,5-Dichloro-4-(n-octyloxy)phenol

187) 3,5-Dichloro-4-(2-(4-chlorobenzyloxy)ethoxy)phenol

188) 4-(2,6-Dichloro-4-hydroxyphenoxy)butyl (2-chloro)benzoate

189) 4-(2,6-Dichloro-4-hydroxyphenoxy)butyl (3-chloro)benzoate

190) 4-(2,6-Dichloro-4-hydroxyphenoxy)butyl (4-chloro)benzoate

191) 4-(2,6-Dichloro-4-hydroxyphenoxy)butyl (4-trifluoromethoxy)benzoate

192) 4-(2,6-Dichloro-4-hydroxyphenoxy)butyl (4-isopropoxy)benzoate

193) 3,5-Dichloro-4-(3-(4-trifluoromethylphenylthio)propyloxy)phenol

194) 3,5-Dichloro-4-(3-(4-tert-butylphenylthio)propyloxy)phenol 195) 3,5-Dichloro-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)phenol

196) 3,5-Dichloro-4-(4-(4-isopropyloxyphenoxy)butyloxy)pheno n_(D) ²⁵.5 1.5484

197) 3,5-Dibromo-4-(2-(4-bromophenyl)ethoxy)phenol n_(D) ²⁶.0 1.5875

198) 3,5-Dibromo-4-(3-(4-chlorophenoxy)propyloxy)phenol m.p. 80.3° C.

199) 3,5-Dibromo-4-(4-phenylbutyloxy)phenol m.p. 80.3° C.

200) 3,5-Dichloro-4-(4-(4-chlorophenyl)butyloxy)phenol

201) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl (3-ethoxy)benzoate

202) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (3-ethoxy)benzoate

203) 4-(2,6-Dichloro-4-hydroxyphenoxy)butyl (3-ethoxy)benzoate

204) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl (4-trifluoromethyl)benzoate

205) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-trifluoromethyl)benzoate

206) 3,5-Dichloro-4-(3-methyl-3-(4-chlorophenoxy)propyloxy)phenol 207) 3,5-Dichloro-4-(1-methyl-3-(4-chlorophenoxy)propyloxy)phenol

208) 3,5-Dichloro-4-(3-methyl-3-butenyloxy)phenol

209) 3,5-Dichloro-4-(3-(4-methoxyphenylthio)propyloxy)phenol

210) 3,5-Dichloro-4-(3-(4-fluorophenylthio)propyloxy)phenol

211) 3,5-Dichloro-4-(3-(2,3,5,6-tetrafluorophenylthio)propyloxy)phenol

212) 3,5-Dichloro-4-(3-(3-chlorophenylthio)propyloxy)phenol

213) 3,5-Dichloro-4-(3-(4-bromophenylthio)propyloxy)phenol

214) 3,5-Dichloro-4-(4-(4-chlorophenoxy)butyloxy)phenol n_(D) ²⁵.0 1.5540

215) 3,5-Dichloro-4-(4-(3-isopropoxyphenoxy)butyloxy)phenol

216) 3,5-Dichloro-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)phenol

217) 3,5-Dichloro-4-(4-(4-(1,1,2,2-tetrafluoroethoxy)phenoxy)butyloxy)phenol

218) 3,5-Dichloro-4-(4-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)butyloxy)phenol

219) 3,5-Dichloro-4-(4-(4-(2,2,2-trifluoroethoxy)phenoxy)butyloxy)phenol

220) 3,5-Dichloro-4-(4-(3-(2,2,2-trifluoroethoxy)phenoxy)butyloxy)phenol

221) 3,5-Dichloro-4-(4-(4-difluoromethoxyphenoxy)butyloxy)phenol

222) 3,5-Dichloro-4-(4-(3-difluoromethoxyphenoxy)butyloxy)phenol

223) 3,5-Dichloro-4-(3-(4-difluoromethoxyphenoxy)propyloxy)phenol

224) 3,5-Dichloro-4-(3-(3-difluoromethoxyphenoxy)butyloxy)phenol

225) 3,5-Dichloro-4-(4-(4-trifluoromethylphenoxy)butyloxy)phenol

226) 3,5-Dichloro-4-(4-(3-trifluoromethylphenoxy)butyloxy)phenol

227) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-chloro)phenylacetate

228) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-chloro)cinnamate

229) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-chloro)phenoxyacetate

230) 3,5-Dichloro-4-(3-(N-methylanilino)propyloxy)phenol

231) 3,5-Dichloro4-(4-(3-fluorophenyl)-3-butenyloxy)phenol

232) 3,5-Dichloro-4-(4-(3-trifluoromethylphenyl)-3-butenyloxy)phenol

233) 3,5-Dichloro-4-(4-(3-trifluoromethoxyphenyl)-3-butenyloxy)phenol

234) 3,5-Dichloro-4-(4-(3-fluorophenyl)butyloxy)phenol

235) 3,5-Dichloro-4-(4-(3-trifluoromethylphenyl)butyloxy)phenol

236) 3,5-Dichloro-4-(4-(3-trifluoromethoxyphenyl)butyloxy)phenol

237) 2-(2,6-Dichloro-4-hydroxyphenoxy)ethyl (4-(2,2,2-trifluoroethoxy))benzoate

238) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-(2,2,2-trifluoroethoxy))benzoate

239) 3,5-Dichloro-4-((3-ethoxycarbonyl)propyloxy)phenol

240) 4-(Trifluoromethoxy)phenoxy 4-(4-hydroxy-2,6-dichlorophenoxy)butyrate

241) 3,5-Dichloro-4-(2-methyl-3-(4-chlorophenoxy)propyloxy)phenol

242) 3-Chloro-5-methyl-4-(3-(4-trifluoromethoxyphenoxy)propyloxy)phenol

243) 3-(2-Chloro-6-methyl-4-hydroxyphenoxy)propyl 4-bromobenzoate

244) 3,5-Dichloro-4-(2-(4-isopropoxyphenyl)ethoxy)phenol

245) 3,5-Dichloro-4-(2-(4-trifluoromethoxyphenyl)ethoxy)phenol

246) 3,5-Dichloro-4-(3-(4-bromophenyl)propyloxy)phenol

247) 3,5-Dichloro-4-(3-(4-trifluoromethylphenyl)propyloxy)phenol

248) 3,5-Dimethyl-4-(3-(4-chlorophenoxy)propyloxy)phenol

249) 3,5-Dichloro-4-(4-(4-chlorophenoxy)-2-(Z)-butenyloxy)phenol

250) 3,5-Dichloro-4-(4-(4-chlorophenoxy)-2-(E)-butenyloxy)phenol

251) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl 4-difluoromethylbenzoate

252) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl 4-(1,1,2,2-tetrafluoroethoxy)benzoate

253) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl 3-methyl-2-(4-chlorophenyl)butyrate

254) 3,5-Dichloro-4-(4-(4-chlorophenylthio)butyloxy)phenol

255) 3,5-Dichloro-4-(4-(4-trifluoromethylphenylthio)butyloxy)phenol

256) 3,5-Dichloro-4-(4-(4-hydroxyphenylthio)butyloxy)phenol

257) 3,5-Dimethyl-4-(3-(4-trifluoromethoxyphenoxy)propyloxy)phenol

258) 3,5-Dichloro-4-(4-(4-methoxyphenylthio)butyloxy)phenol

259) 3,5-Dichloro-4-(4-(4-isopropoxyphenylthio)butyloxy)phenol

260) 3,5-Dichloro-4-(3-(4-chlorophenylsulfenyl)propyloxy)phenol

261) 3,5-Dichloro-4-(4-(4-chlorophenoxy)butyloxy)phenol

262) 3,5-Diisopropyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)phenol

263) 3,5-Diethyl-4-(3-(4-trifluoromethoxyphenoxy)propyloxy)phenol n_(D) ²⁰.4 1.5060

264) 3-Ethyl-5-methyl-4-(3-(4-trifluoromethoxyphenoxy)propyloxy)phenol n_(D) ²⁵.4 1.4955

265) 3-(2,6-Dichloro-4-hydroxyphenoxy)propyl (4-trifluoromethyl)cinnamate

266) 3,5-Dichloro-4-(3-(4-trifluoromethoxyanilino)propyloxy)phenol

267) 3,5-Dichloro-4-(3-anilino)propyloxy)phenol

268) 3,5-Dichloro-4-(3-(4-trifluoromethylanilino)propyloxy)phenol

269) 3,5-Dichloro-4-(3-(N-methyl -4-trifluoromethylanilino)propyloxy)phenol

270) 3,5-Dichloro-4-(3-(N-acyl-4-trifluoromethylanilino)propyloxy)phenol

271) 3,5-Dichloro-4-(3-(4trifluoromethoxyphenylthio)propyloxy)phenol

272) 3,5-Dichloro-4-(4-trifluoromethylbenzyloxy)thiophenol

273) 3,5-Dichloro-4-(2-(4-trifluoromethylphenyl)ethoxy)phenol

274) 3,5-Dichloro-4-(3-(4-trifluoromethylphenyl)propyloxy)phenol

275) 3,5-Dichloro-4-(3-(4-trifluoromethylphenoxy)propyloxy)phenol

276) 3-Ethyl-5-methyl-4-(3-(4-trifluoromethylphenoxy)propyloxy)phenol

277) 3,5-Dichloro-4-(3-(4-chlorophenylsulfonyl)propyloxy)phenol

278) 2,3,5,6-Tetrachloro-4-(3-(4-trifluoromethylphenoxy)propyloxy)phenol

279) 3,5-Dichloro-4-(4-anilino)butyloxy)phenol

280) 3,5-Dichloro-4-(4-(4-trifluoromethylanilino)butyloxy)phenol

281) 3,5-Dichloro-4-(4-(4-trifluoromethoxyanilino)butyloxy)phenol

282) 3,5-Diethyl-4-(3-(4-trifluoromethylphenoxy)propyloxy)phenol

283) 3,5-Dichloro-4-(3-(4-isopropoxycarbonylphenoxy)propyloxy)phenol

284) 3,5-Dichloro-4-(3-(4-methoxycarbonylphenoxy)propyloxy)phenol

285) 3-Chloro-5-methyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)phenol

286) 3-Chloro-5-methyl-4-(4-(4-trifluoromethylphenoxy)butyloxy)phenol

287) 3-Chloro-5-methyl-4-(4-(4-chlorophenoxy)butyloxy)phenol

288) 3-Chloro-5-methyl-4-(3-(4-bromophenoxy)propyloxy)phenol

289) 3-Chloro-5-methyl-4-(4-(4-bromophenoxy)butyloxy)phenol

290) 3-Chloro-5-methyl-4-(3-(4-isopropoxyphenoxy)propyloxy)phenol

291) 3-Chloro-5-methyl-4-(4-(4-isopropoxyphenoxy)butyloxy)phenol

292) 3-Ethyl-5-methyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)phenol

293) 3-Ethyl-5-methyl-4-(4-(4-trifluoromethylphenoxy)butyloxy)phenol

294) 3-Ethyl-5-methyl-4-(3-(4-chlorophenoxy)propyloxy)phenol

295) 3-Ethyl-5-methyl-4-(4-(4-chlorophenoxy)butyloxy)phenol

296) 3-Ethyl-5-methyl-4-(3-(4-bromophenoxy)propyloxy)phenol

297) 3-Ethyl-5-methyl-4-(4-(4-bromophenoxy)butyloxy)phenol

298) 3-Ethyl-5-methyl-4-(3-(4-isopropoxyphenoxy)propyloxy)phenol

299) 3-Ethyl-5-methyl-4-(4-(4-isopropoxyphenoxy)butyloxy)phenol

300) 3,5-Diethyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)phenol

301) 3,5-Diethyl-4-(4-(4-trifluoromethylphenoxy)butyloxy)phenol

302) 3,5-Diethyl-4-(3-(4-chlorophenoxy)propyloxy)phenol

303) 3,5-Diethyl-4-(4-(4-chlorophenoxy)butyloxy)phenol

304) 3,5-Diethyl-4-(3-(4-bromophenoxy)propyloxy)phenol

305) 3,5-Diethyl-4-(4-(4-bromophenoxy)butyloxy)phenol

306) 3,5-Diethyl-4-(3-(4-isopropoxyphenoxy)propyloxy)phenol

307) 3,5-Diethyl-4-(4-(4-isopropoxyphenoxy)butyloxy)phenol

308) 3,5-Diisopropyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)phenol

309) 3,5-Diisopropyl-4-(3-(4-trifluoromethoxyphenoxy)propyloxy)phenol

310) 3,5-Diisopropyl-4-(4-(4-trifluoromethoxyphenoxy)butyloxy)phenol

311) 3,5-Diisopropyl-4-(3-(4-chlorophenoxy)propyloxy)phenol

312) 3,5-Diisopropyl-4-(4-(4-chlorophenoxy)butyloxy)phenol

313) 3,5-Diisopropyl-4-(3-(4-bromophenoxy)propyloxy)phenol

314) 3,5-Diisopropyl-4-(4-(4-bromophenoxy)butyloxy)phenol

315) 3,5-Diisopropyl-4-(3-(4-isopropoxyphenoxy)propyloxy)phenol

316) 3,5-Diisopropyl-4-(4-(4-isopropoxyphenoxy)butyloxy)phenol

The following is a production example for the intermediate compound of the general formula IX!.

Intermediate Production Example 5 Production of 4-(2-chlorobenzyloxy)-3,5-dichlorophenoxyacetaldehyde

A mixture of 0.85 g of 4-(2-chlorobenzyloxy)-3,5-dichlorophenol, 0.47 ml of bromoacetaldehyde diethyl acetal, 0.46 g of potassium carbonate and 20 ml of N,N-dimethylformamide was stirred at 90° C. for 6 hours. After cooling to room temperature, the reaction mixture was poured into ice water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, and dried with anhydrous magnesium sulfate, followed by removal of the solvent by distillation under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 0.85 g of 4-(2-chlorobenzyloxy)-3,5-dichlorophenoxyacetaldehyde diethyl acetal (72% yield).

Then, 0.85 g of 4-(2-chlorobenzyloxy)-3,5-dichlorophenoxyacetaldehyde diethyl acetal was dissolved in 10 ml of acetic acid, to which 1 ml of concentrated hydrochloric acid was added dropwise, while stirring under ice cooling. After stirring under ice cooling for 2 hours, the reaction mixture was poured into ice water, and extracted twice with diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, followed by removal of the solvent by distillation under reduced pressure, which afforded 0.70 g of 4-(2-chlorobenzyloxy)-3,5-dichlorophenoxyacetaldehyde in crude form.

The following are production examples for the intermediate compounds of the general formula III! or X!.

Intermediate Production Example 6 Production of Intermediate Compound 317)

A reaction vessel was charged with 30.5 g of 4-hydroxyphenyl benzoate, 21.6 g of potassium carbonate, 20.8 g of 1,1,3-trichloropropene and 100 ml of N,N-dimethylformamide. After stirring at room temperature for 15 hours, the reaction mixture was poured into water, and extracted twice with 150 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 44.1 g of 4-(3,3-dichloro-2-propenyloxy)phenyl benzoate (96% yield).

A reaction vessel was charged with 44.1 g of 4-(3,3-dichloro-2-propenyloxy)phenyl benzoate and 400 ml of methanol, to which 33 g of 30% potassium hydroxide was slowly added dropwise under ice cooling. After stirring for 1 hour, the reaction mixture was made weakly acidic by the addition of 10% hydrochloric acid, and extracted twice with 150 ml of diethyl ether under salting out. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 26.0 g of 4-(3,3-dichloro-2-propenyloxy)phenol (87% yield).

A reaction vessel was charged with 26.0 g of 4-(3,3-dichloro-2-propenyloxy)phenyl and 500 ml of carbon tetrachloride, to which a solution of 27.1 g of tert-butyl hypochlorite dissolved in 20 ml of carbon tetrachloride was slowly added dropwise, while stirring under ice cooling. After 24 hours, the reaction mixture was poured into water, followed by phase separation. The organic layer (i.e., carbon tetrachloride layer) was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 11.0 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol (32% yield), n_(D) ²².5 1.5895.

Intermediate Production Example 7 Production of Intermediate Compound 325)

A solution of 50 g of 4-bromo-6-chloro-2-methylphenol and 42.5 g of benzyl bromide dissolved in 200 ml of N,N-dimethylformamide was stirred at room temperature, to which 37.4 g of potassium carbonate was added, and the mixture was stirred for 12 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was added to 400 ml of diethyl ether, washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 63 g of 4-bromo-6-chloro-2-methyl-1-benzyloxybenzene (90% yield).

Then, 40 g of 4-bromo-6-chloro-2-methyl-1-benzyloxybenzene was dissolved in 400 ml of tetrahydrofuran, followed by stirring at -70° C., to which 76 ml of n-butyl lithium solution (in hexane, 1.69 mol/liter) was added dropwise, followed by further stirring at -70° C. for 2 hours. To this reaction mixture was added dropwise a solution of 13.3 g of trimethoxyborane dissolved in 50 ml of tetrahydrofuran. Then, the reaction mixture was stirred for 1 hours, while warming to room temperature, and 100 ml of 10% aqueous hydrochloric acid solution was added in small portions, followed by stirring for 20 minutes. The tetrahydrofuran layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated. The residue was mixed with 200 ml of toluene, and heated at 70° C. under stirring, to which 36 ml of 30% aqueous hydrogen peroxide solution was added dropwise. After heating under reflux for 1 hour, the reaction mixture was washed once with water, twice with 10% aqueous ammonium ferrous sulfate solution, and once with water, followed by phase separation. The toluene layer was dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 29 g of 4-benzyloxy-3-chloro-5-methylphenol (91% yield).

To a solution of 27.3 g of 4-benzyloxy-3-chloro-5-methylphenol dissolved in 250 ml of chloroform and stirred at 0° C. were added 15.4 g of benzoyl chloride and then 13.3 g of triethylamine. After stirring at room temperature for 2 hours, the chloroform layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel chromatography, which afforded 35 g of 4-benzyloxy-3-chloro-5-methyl-1-benzoyloxybenzene (90% yield).

A reaction vessel was charged with 35 g of 4-benzyloxy-3-chloro-5-methyl-1-benzoyloxybenzene and 200 ml of ethyl acetate, and the air in the vessel was replaced with nitrogen. Then, 2 g of 10% palladium carbon was added, and the nitrogen in the vessel was replaced with hydrogen, followed by vigorous stirring at room temperature for 10 hours. The hydrogen in the vessel was replaced with nitrogen, after which the reaction mixture was filtered, and the filtrate was concentrated. The residue was silica gel chromatography was subjected to silica gel chromatography, which afforded 25 g of 4-benzoyloxy-2-chloro-6-methylphenol (96% yield).

Then, 25 g of 4-benzoyloxy-2-chloro-6-methylphenol was dissolved in 250 ml of chloroform, to which 12 g of chloromethyl methyl ether was added, while stirring at 0° C., and 21 g of N-ethyldiisopropylamine was added dropwise. After heating under reflux for 1 hour, the chloroform layer was washed with water, and concentrated. The residue was subjected to silica gel chromatography, which afforded 27.4 g of 3-chloro4-methoxymethoxy-5-methyl-1-benzoyloxybenzene (96% yield).

Then, 26 g of 3-chloro-4-methoxymethoxy-5-methyl-1-benzoyloxybenzene was dissolved in 200 ml of methanol, and the solution was stirred at room temperature, while adding dropwise 60 ml of 10% aqueous potassium hydroxide solution. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was added to 150 ml of water, neutralized with 10% aqueous hydrochloric acid solution, and extracted with 200 ml of diethyl ether. The solvent was removed by distillation under reduced pressure, and the residue was subjected to silica gel chromatography, which afforded 17.4 g of 3-chloro-4-methoxymethoxy-5-methylphenol (96% yield).

To a mixture of 10 g of 3-chloro-4-methoxymethoxy-5-methylphenol, 7 g of potassium carbonate and 100 ml of N,N-dimethylformamide was added dropwise a solution of 8 g of 1,1,3-trichloro-1-propene dissolved in 30 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was poured into ice water, and extracted with 200 ml of diethyl ether. The combined ether was washed with water, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel chromatography, which afforded 14.1 g of 3-chloro-4-methoxymethoxy-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzene (91% yield).

Then, 14.1 g of 3-chloro-4-methoxymethoxy-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzene was dissolved in 100 ml of 80% aqueous acetic acid solution, followed by heating under reflux with stirring for 1 hour. After completion of the reaction, the reaction mixture was mixed with 200 ml of water, and extracted twice with 200 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel chromatography, which afforded 11.3 g of 2-chloro-6-methyl-(3,3-dichloro-2-propenyloxy)phenol (93% yield), m.p. 70.0° C.

The following are specific examples of the intermediate compounds of the general formula III! or X! under the corresponding compound numbers with their physical properties, if measured.

317) 2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenol

¹ H-NMR (CDCl₃ /TMS) δ(ppm): 4.57 (2H, d), 5.50 (1H, brs), 6.11 (1H, t), 6.85 (2H, s)

318) 2,6-Dichloro-4-(3,3-dibromo-2-propenyloxy)phenol

319) 2-Chloro-6-bromo-4-(3,3-dichloro-2-propenyloxy)phenol

320) 2-Chloro-6-bromo-4-(3,3-dibromo-2-propenyloxy)phenol

321) 2,6-Dibromo-4-(3,3-dichloro-2-propenyloxy)phenol

322) 2,6-Dibromo-4-(3,3-dibromo-2-propenyloxy)phenol

323) 2,6-Dimethyl-4-(3,3-dichloro-2-propenyloxy)phenol

324) 2,6-Dimethyl-4-(3,3-dibromo-2-propenyloxy)phenol

325) 2-Chloro-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenol m.p. 70.0° C.

326) 2-Chloro-6-methyl-4-(3,3-dibromo-2-propenyloxy)phenol

327) 2,6-Diethyl-4-(3,3-dichloro-2-propenyloxy)phenol

328) 2,6-Diethyl-4-(3,3-dibromo-2-propenyloxy)phenol

329) 2,6-Diisopropyl-4-(3,3-dichloro-2-propenyloxy)phenol

330) 2,6-Diisopropyl-4-(3,3-dibromo-2-propenyloxy)phenol 331) 2-Ethyl-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenol

332) 2-Ethyl-6-methyl-4-(3,3-dibromo-2-propenyloxy)phenol

333) 2-Ethyl-6-chloro-4-(3,3-dichloro-2-propenyloxy)phenol

334) 2-Ethyl-6-chloro-4-(3,3-dibromo-2-propenyloxy)phenol

335) 2,6-Difluoro-4-(3,3-dichloro-2-propenyloxy)phenol

336) 2,6-Difluoro-4-(3,3-dibromo-2-propenyloxy)phenol

337) 2-Chloro-6-fluoro-4-(3,3-dichloro-2-propenyloxy)phenol

338) 2-Chloro-6-fluoro-4-(3,3-dibromo-2-propenyloxy)phenol

339) 2-Isopropyl-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenol

340) 2-Isopropyl-6-methyl-4-(3,3-dibromo-2-propenyloxy)phenol

341) 2-Isopropyl-6-ethyl-4-(3,3-dichloro-2-propenyloxy)phenol

342) 2-Isopropyl-6-ethyl-4-(3,3-dibromo-2-propenyloxy)phenol

343) 2-Isopropyl-6-chloro-4-(3,3-dichloro-2-propenyloxy)phenol

344) 2-Isopropyl-6-chloro-4-(3,3-dibromo-2-propenyloxy)phenol

345) 2-Bromo-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenol

346) 2-Bromo-6-methyl-4-(3,3-dibromo-2-propenyloxy)phenol

347) 2-Bromo-6-ethyl-4-(3,3-dichloro-2-propenyloxy)phenol

348) 2-Bromo-6-ethyl-4-(3,3-dibromo-2-propenyloxy)phenol

349) 2-Bromo-6-isopropyl-4-(3,3-dichloro-2-propenyloxy)phenol

350) 2-Bromo-6-isopropyl-4-(3,3-dibromo-2-propenyloxy)phenol

351) 2-Fluoro-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenol

352) 2-Fluoro-6-methyl-4-(3,3-dibromo-2-propenyloxy)phenol

353) 2-Fluoro-6-ethyl-4-(3,3-dichloro-2-propenyloxy)phenol

354) 2-Fluoro-6-ethyl-4-(3,3-dibromo-2-propenyloxy)phenol

355) 2-Fluoro-6-isopropyl-4-(3,3-dichloro-2-propenyloxy)phenol

356) 2-Fluoro-6-isopropyl-4-(3,3-dibromo-2-propenyloxy)phenol

357) 2-Bromo-6-fluoro-4-(3,3-dichloro-2-propenyloxy)phenol

358) 2-Bromo-6-fluoro-4-(3,3-dibromo-2-propenyloxy)phenol

359) 2-Chloro-6-trifluoromethyl-4-(3,3-dichloro-2-propenyloxy)phenol

360) 2-Chloro-6-trifluoromethyl-4-(3,3-dibromo-2-propenyloxy)phenol

361) 2-Fluoro-6-trifluoromethyl-4-(3,3-dichloro-2-propenyloxy)phenol

362) 2-Fluoro-6-trifluoromethyl-4-(3,3-dibromo-2-propenyloxy)phenol

The following are production examples for the intermediate compounds of general formula II! or XIII!.

Intermediate Production Example 8 Production of intermediate compound 363)

A reaction vessel was charged with 10.6 g of 1,3-dibromopropane, 5.53 g of potassium carbonate and 100 ml of N,N-dimethylformamide, to which a solution of 30.5 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol dissolved in 40 ml of N,N-dimethylformamide was slowly added dropwise. After stirring at room temperature for 24 hours, the reaction mixture was poured into water, and extracted twice with 150 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 11.1 g of 3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (77% yield), n_(D) ²⁴.0 1.5693.

Intermediate Production Example 9 Production of Intermediate Compound 365)

A reaction vessel was charged with 22.67 g of 1,4-dibromobutane, 11.06 g of potassium carbonate and 200 ml of N,N-dimethylformamide, to which a solution of 20.16 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol dissolved in 80 ml of N,N-dimethylformamide was slowly added dropwise. After stirring at room temperature for 24 hours, the reaction mixture was poured into water, and extracted twice with 300 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 21.7 g of 3,5-dichloro-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (74% yield), n_(D) ²⁵.0 1.5666.

The following are production examples for the intermediate compounds of general formula II! or XIV!.

Intermediate Production Example 10 Production of Intermediate Compound 367)

A reaction vessel was charged with 1.l g of 3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 3.31 g of benzoic acid, 3.90 g of potassium carbonate and 50 ml of N,N-dimethylformamide. After stirring at room temperature for 24 hours, the reaction mixture was poured into water, and extracted twice with 150 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 11.6 g, of 3,5-dichloro-4-(3-benzoyloxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (95% yield).

A reaction vessel was charged with 11.6 g of 3,5-dichloro-4-(3-benzoyloxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 15.2 g of 10% aqueous potassium hydroxide solution and 300 ml of methanol. After stirring at room temperature for 24 hours, and the reaction mixture was concentrated. The concentrate was poured into water, and extracted twice with 150 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 7.41 g of 3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-1-propyl alcohol (83%o yield), m.p. 56.6° C.

The following are specific examples of the intermediate compounds of the general formula II!, XIII! or XIV! under the corresponding compound numbers with their physical properties, if measured.

363) 3,5-Dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n.sub.D²⁴.0 1.5693

364) 3,5-Dichloro-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

365) 3,5-Dichloro-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene n_(D) ²².5 1.5666

366) 3,5-Dichloro-4-(4-chlorobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

367) 3,5-Dichloro-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene m.p. 56.6° C.

368) 3,5-Dichloro-4-(3-hydroxybutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

369) 3,5-Dichloro-4-(3-bromopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

370) 3,5-Dichloro-4-(3-chloropropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

371) 3,5-Dichloro-4-(4-bromobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

372) 3,5-Dichloro-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

373) 3,5-Dichloro-4-(3-hydroxypropyloxy)-1-(3,3-dibromo -2-propenyloxy)benzene m.p. 56.6° C.

374) 3,5-Dichloro-4-(4-hydroxybutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

375) 3-Chloro-5-methyl-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

376) 3-Chloro-5-methyl-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

377) 3-Chloro-5-methyl-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzen

378) 3-Chloro-5-methyl-4-(4-chlorobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

379) 3-Chloro-5-methyl-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

380) 3-Chloro-5-methyl-4-(4-hydroxybutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

381) 3-Chloro-5-methyl-4-(3-bromopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

382) 3 -Chloro-5-methyl-4-(3-chloropropyloxy 1-(3,3-dibromo-2-propenyloxy)benzene

383) 3-Chloro-5-methyl-4-(4-bromobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

384) 3-Chloro-5-methyl-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

385) 3-Chloro -5-methyl-4-(3-hydroxypropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

386) 3-Chloro-5-methyl-4-(4-hydroxybutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

387) 3-Ethyl-5-methyl-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

388) 3-Ethyl-5-methyl-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

389) 3-Ethyl-5-methyl-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

390) 3-Ethyl-5-methyl-4-(4-chlorobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

391) 3-Ethyl-5-methyl-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

392) 3-Ethyl-5-methyl-4-(4-hydroxybutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

393) 3-Ethyl-5-methyl-4-(3-bromopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

394) 3-Ethyl-5-methyl-4-(3-chloropropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

395) 3-Ethyl-5-methyl -4-(3-bromobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

396) 3-Ethyl-5-methyl-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

397) 3-Ethyl-5-methyl-4-(3-hydroxy propyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

398) 3-Ethyl-5-methyl-4-(4-hydroxybutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

399) 3,5-Dibromo-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

400) 3,5-Dibromo-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

401) 3,5-Dibromo-4-(3-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

402) 3,5-Dibromo -4-(4-chlorobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

403) 3,5-Dibromo-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

404) 3,5-Dibromo-4-(4-hydroxybutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

405) 3,5-Dibromo-4-(3-bromopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

406) 3,5-Dibromo-4-(3-chloropropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

407) 3,5-Dibromo-4-(4-bromobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

408) 3,5-Dibromo-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

409) 3,5-Dibromo-4-(3-hydroxypropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

410) 3,5-Dibromo-4-(4-hydroxybutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

411) 3,5-Dimethyl-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

412) 3,5-Dimethyl-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

413) 3,5-Dimethyl-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

414) 3,5-Dimethyl-4-(4-chlorobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

415) 3,5-Dimethyl-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

416) 3,5-Dimethyl-4(4-hydroxybutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

417) 3,5-Dimethyl-4-(3-bromopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

418) 3,5-Dimethyl-4-(3-chloropropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

419) 3,5-Dimethyl-4-(4-bromobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

420) 3,5-Dimethyl-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

421) 3,5-Dimethyl-4-(3-hydroxypropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

422) 3,5-Dimethyl-4-(4-hydroxybutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

423) 3,5-Diethyl -4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

424) 3,5-Diethyl-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

425) 3,5-Diethyl-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

426) 3,5-Diethyl-4-(34-chlorobutyloxy)-1-(3,3-dichloro-2-propenyloxy)-benzene

427) 3,5-Diethyl-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

428) 3,5-Diethyl-4-(4-hydroxy butyloxy))-1-(3,3-dichloro-2-propenyloxy)benzene

429) 3,5-Diethyl-4-(3-bromopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

430) 3,5-Diethyl -4-(3-chloropropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

431) 3,5-Diethyl -4-(4-bromobutyloxy)-l1-(3,3-dibromo-2-propenyloxy)benzene

432) 3,5-Diethyl-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

433) 3,5-Diethyl-4-(3-hydroxypropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

434) 3,5-Diethyl-4-(4-hydroxybutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

435) 3,5-Diisopropyl-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

436) 3,5-Diisopropyl-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

437) 3,5-Diisopropyl -4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

438) 3,5-Diisopropyl-4-(4-chlorobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

439) 3,5-Diisopropyl-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

440) 3,5-Diisopropyl-4-(4-hydroxybutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

441) 3,5-Diisopropyl-4-(3-bromopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

442) 3,5-Diisopropyl-4-(3-chloropropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

443) 3,5-Diisopropyl-4-(4-bromobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

444) 3,5-Diisopropyl-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

445) 3,5-Diisopropyl-4-(3-hydroxypropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

446) 3,5-Diisopropyl-4-(4-hydroxybutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

447) 3,5-Difluoro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

448) 3,5-Difluoro-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

449) 3,5-Difluoro-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

450) 3,5-Difluoro-4-(4-chlorobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

451) 3,5-Difluoro-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

452) 3,5-Difluoro-4-(4-hydroxybutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

453) 3,5-Difluoro-4-(3-bromopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

454) 3,5-Difluoro-4-(3-chloropropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

455) 3,5-Difluoro-4-(4-bromobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

456) 3,5-Difluoro-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

457) 3,5-Difluoro-4-(3-hydroxypropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

458) 3,5-Difluoro-4-(4-hydroxybutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

459) 3-Chloro-5-fluoro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

460) 3-Chloro-5-fluoro-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

461) 3-Chloro-5-fluoro-4-(4-bromo butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

462) 3-Chloro-5-fluoro-4-(4-chlorobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

463) 3-Chloro-5-fluoro-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

464) 3-Chloro-5-fluoro-4-(4-hydroxybutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

465) 3-Chloro-5-fluoro-4-(3-bromopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

466) 3-Chloro-5-fluoro-4-(3-chloropropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

467) 3-Chloro -5-fluoro-4-(4-bromobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

468) 3-Chloro-5-fluoro-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

469) 3-Chloro-5-fluoro-4-(3-hydroxypropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

470) 3-Chloro-5-fluoro-4-(4-hydroxybutyloxy 1-(3,3-dibromo-2-propenyloxy)benzene

471) 3-Bromo-5-chloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

472) 3-Bromo-5-chloro-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

473) 3-Bromo-5-chloro-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

474) 3-Bromo -5-chloro-4-(4-chloro butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

475) 3-Bromo -5-chloro-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

476) 3-Bromo-5-chloro-4-(4-hydroxybutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

477) 3-Bromo-5chloro-4-(3-bromopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

478) 3-Bromo-5-chloro-4-(3-chloropropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

479) 3-Bromo-5-chloro-4-(4-bromobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

480) 3-Bromo-5-chloro-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

481) 3-Bromo -5-chloro -4-(3-hydroxypropyloxy)-1-(3,3-dibromo -2-propenyloxy)benzene

482) 3-Bromo-5-chloro -4-(3-hydroxybutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

483) 3-Chloro -5-ethyl-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

484) 3-Chloro-5-ethyl-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

485) 3-Chloro-5-ethyl-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

486) 3-Chloro-5-ethyl-4-(4-chlorobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

487) 3-Chloro-5-ethyl-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

488) 3-Chloro-5-ethyl-4-(4-hydroxybutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

489) 3-Chloro-5-ethyl-4-(3-bromopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

490) 3-Chloro -5-ethyl-4-(3-chloropropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

491) 3-Chloro-5-ethyl-1-4-(4-bromobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

492) 3-Chloro-5-ethyl-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

493) 3-Chloro-5-ethyl-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

494) 3-Chloro-5-ethyl-4-(4-hydroxybutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

495) 3-Chloro-5-isopropyl-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

496) 3-Chloro-5-isopropyl-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene 497) 3-Chloro-5-isopropyl-4-(4-bromobutyloxy)-1-(3,3-dichloro -2-propenyloxy)benzene

498) 3-Chloro-5-isopropyl-4-(4-chlorobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

499) 3-Chloro-5-isopropyl-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

500) 3-Chloro-5-isopropyl-4-(4-hydroxy butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

501) 3-Chloro-5-isopropyl -4-(3-bromopropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

502) 3-Chloro-5-isopropyl-4-(3-chloropropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

503) 3-Chloro-5-isopropyl-4-(4-bromobutyloxy)-1-(3,3-dibromo -2-propenyloxy)benzene

504) 3-Chloro-5-isopropyl-4-(4-chlorobutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

505) 3-Chloro-5-isopropyl-4-(3-hydroxypropyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

506) 3-Chloro-5-isopropyl-4-(4-hydroxybutyloxy)-1-(3,3-dibromo-2-propenyloxy)benzene

The following are formulation examples in which "parts" are by weight and the present compounds are designated by the corresponding compound numbers as described above.

Formulation Example 1 Emulsifiable Concentrates

Ten parts of each of the present compounds (1) to (325) are dissolved in 35 parts of xylene and 35 parts of N,N-dimethylformamide, to which 14 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added, and the mixture is well stirred to give a 10% emulsifiable concentrate of each compound.

Formulation Example 2 Wettable Powders

Twenty parts of each of the present compounds (1) to (325) are added to a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrated silicon oxide fine powder and 54 parts of diatomaceous earth, and the mixture is stirred with a mixer to give a 20% wettable powder of each compound.

Formulation Example 3 Granules

To 5 parts of each of the present compounds (1) to (325) are added 5 parts of synthetic hydrated silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 55 parts of clay, and the mixture is well stirred. Then, a suitable amount of water is added to the mixture, which is further stirred, granulated with a granulator and then air-dried to give a 5% granule of each compound.

Formulation Example 4 Dusts

One part of each of the present compounds (1) to (325) is dissolved in a suitable amount of acetone, to which 5 parts of synthetic hydrated silicon oxide fine powder, 0.3 part of PAP and 93.7 parts of clay are added, and the mixture is stirred with a mixer. The removal of acetone by evaporation gives a I% dust of each compound.

Formulation Example 5 Flowables

Twenty parts of each of the present compounds (1) to (325) are mixed with 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and the mixture is pulverized into fine particles having a particle size of not more than 3 μm with a sand grinder, to which 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate are added and then 10 parts of propylene glycol are added. The mixture is stirred to give a 20% water-based suspension of each compound.

Formulation Example 6 Oil Solutions

First, 0.1 part of each of the present compounds (1) to (325) is dissolved in 5 parts of xylene and 5 parts of trichloroethane. Then, the solution was mixed with 89.9 parts of deodorized kerosine to give a 0. 1% oil solution of each compound.

Formulation Example 7 Oil-based Aerosols

First, 0.1 part of each of the present compounds (1) to (325), 0.2 part of tetramethrin, 0.1 part of d-phenothrin, and 10 parts of trichloroethane are dissolved in 59.6 parts of deodorized kerosine, and the solution is put in an aerozol vessel. Then, the vessel is equipped with a valve, through which 30 parts of a propellant (liquefied petroleum gas) are charged under increased pressure to give an oil-based aerosol of each compound.

Formulation Example 8 Water-based Aerosols

An aerosol vessel is filled with 50 parts of pure water and a mixture of 0.2 part of each of the present compounds (1) to (325), 0.2 part of d-allethrin, 0.2 part of d-phenothrin, 5 parts of xylene, 3.4 parts of deodorized kerosine and 1 part of an emulsifier ATMOS 300 (registered trade name by Atlas Chemical Co.)!. Then, the vessel is equipped with a valve, through which 40 parts of a propellant (liquefied petroleum gas) are charged under pressure to give a water-based aerosol of each compound.

Formulation Example 9 Mosquito-coils

First, 0.3 g of each of the present compounds (1) to (325) is mixed with 0.3 g of d-allethrin, and the mixture is dissolved in 20 ml of acetone. The solution is uniformly mixed with 99.4 g of a carrier for mosquito-coils (prepared by mixing Tabu powder, pyrethrum marc powder and wood flour in the ratio of 4:3:3) under stirring. The mixture is well kneaded with 120 ml of water, molded and dried to give a mosquito-coil of each compound.

Formulation Example 10 Electric Mosquito-mats

First, 0.4 g of each of the present compounds (1) to (325), 0.4 parts of d-allethrin and 0.4 g of pipenyl butoxide are dissolved in acetone to have a total volume of 10 ml. Then, 0.5 ml of the solution is uniformly absorbed in a substrate for electric mosquito-mats having a size of 2.5 cm×1.5 cm×0.3 cm (prepared by forming a fibrillated mixture of cotton linter and pulp into a sheet) to give an electric mosquito-mat of each compound.

Formulation Example 11 Heating Smoke Formulations

First, 100 mg of each of the present compounds (1) to (325) is dissolved in a suitable amount of acetone. Then, the solution is absorbed in a porous ceramic plate having a size of 4.0 cm×4.0 cm×1.2 cm to give a heating smoke formulation of each compound.

Formulation Example 12 Poison Baits

First, 10 mg of each of the present compounds (1) to (325) is dissolved in 0.5 ml of acetone, and the solution is uniformly mixed with 5 g of solid bait powder for animals (Breeding Solid Feed Powder CE-2, trade name by Japan Clea Co., Ltd.). Then, the removal of acetone by air drying gives a 0.5% poison bait of each compound.

The following Test Examples demonstrate that the present compounds are useful as an active ingredient of insecticidal/acaricidal agents. In these Test Examples, the present compounds are designated by the corresponding compound numbers as described above and the compounds used for comparison are designated by the corresponding compound symbols as shown in Table 18.

                                      TABLE 18     __________________________________________________________________________     Compound            Chemical structure Remarks     __________________________________________________________________________     (A)             ##STR200##        Compound disclosed in JP-A 48-86835/1973     (B)             ##STR201##        Compound disclosed in JP-A 49-1526/1974     __________________________________________________________________________

Test Example 1 Insecticidal Test Against Spodoptera litura

A 200-fold dilution containing an active ingredient at 500 ppm, which had been prepared by diluting with water an emulsifiable concentrate of the test compound obtained according to Formulation Example 1, was absorbed at a volume of 2 ml in 13 g of an artificial diet for Spodoptera litura, which had been prepared in a polyethylene cup having a diameter of 11 cm. Ten fourth-instar larvae of Spodoptera litura were set free in the cup. After 6 days, the survival of larvae was examined to determine the mortality. The test was conducted in duplicate.

As a result, it was found that the present compounds (1)-(39), (41)-(49), (51)-(66), (68)-(72), (74)-(86), (88)-(101), (104)-(172), (174)-(189), (191), (193)-(200), (202)-(246), (248), (250)-(274), (276)-(279), (284)-(286) and (288)-(308) exhibited the mortality of 80% or more. In contrast, both compounds (A) and (B) for comparison exhibited the mortality of 0%.

Test Example 2 Test Against Tetranychus urticae Koch

Ten female adults of Tetranychus urticae Koch per one leaf were allowed to parasitize to a potting bean at the primary leaf stage harvested for 7 days after seeding, and these pots were placed in a thermostated room at 25° C. After 6 days, a chemical solution containing an active ingredient at 500 ppm, which had been prepared by diluting with water an emulsifiable concentrate of the test compound obtained according to Formulation Example 1, was sprayed at a volume of 15 ml over each pot on a turntable. At the same time, 2 ml of the same solution was drenched in the soil. After 8 days, the degree of damage on the respective plants caused by Tetranychus urticae Koch was examined. The effects were determined according to the following criteria:

-: Damage is scarcely observed.

+: Damage is slightly observed.

++: Damage is observed at the same level as in the non-treated field.

As a result, it was found that the present compounds (7)-(8), (25)-(27), (42)-(43), (49), (63), (69)-(72), (76), (77), (102), (104), (119), (120) and evaluated as "-" or "+". In the contrast, both compounds A and B for comparison were evaluated as "++".

Test Example 3 Insecticidal Test Against Heliothis virescens

A dilution containing an active ingredient at 100 ppm, which had been prepared by diluting with water an emulsifiable concentrate of the test compound obtained according to Formulation Example 1, was incorporated at a volume of 0.2 ml in an artificial diet. Some second-instar larvae of H. virescens were given the diet and bred in a plastic vessel. After 6-7 days, the mortality was determined.

As a result, it was found that the present compounds (27), (34), (35), (42), (43), (54)-(57), (60), (64), (65), (68)-(70), (77), (81), (84)-(86), (88-(92), 98)-(101), (107), (108), (112), (114)-(116), (119), (122), (124), (125), (127)-(129(146), (147), (164), (166), (185), (202), (203), (222), (224)-(226), (229), (233), (262), (263) and (272) exhibited the mortality of 80% or more. In contrast, both compounds (A) and (B) for comparison exhibited the mortality of 0%.

Test Example 4 Insecticidal Test Against Plutella xylostella

A chemical solution containing an active ingredient at 50 ppm, which had been prepared by diluting an emulsifiable concentrate of the test compound obtained according to Formulation Example 1 with water containing spreading agent RINOU (Nihon Nouyaku K.K.) to a degree such that the spreading agent had been 1000-fold diluted, was sprayed at a volume 25 ml over each pot of a potting cabbage at the five leaf stage. The treated plants were air dried, on which ten third-instar larvae of Plutella xylostella were set free. After 4 days, the mortality was determined.

As a result, it was found that the present compounds (27), (63)-(65), (68), (70), (77), (81), (84), (98), (100), (101), (106), (108), (111), (120), (130), (139)-(142), (145)-(147), (149)-(153), (157)-(159), (162), (164)-(166), (185), (188), (199), (202)-(204), (209), (212), (214), 9216), (222)-(234), (236), (242), (246(250), (251), (259), (260), (262), (263), (267), (272), (284), (292), (294)-(296), (299)-(302), (304), (306) and (308) exhibited the mortality of 80% or more. In contrast, both compounds (A) and (B) for comparison exhibited the mortality of 0%.

Industrial Applicability

The present compounds have excellent insecticidal/acaricidal activity, so that they are satisfactorily active for the control of noxious insects, mites and ticks. 

We claim:
 1. A dihalopropene compound of the general formula: ##STR202## wherein R¹ is C₁ -C₁₀ alkyl, C₁ -C₅ haloalkyl, C₂ -C₁₀ alkenyl, C₂ -C₆ haloalkenyl, C₃ -C₉ alkynyl, C₃ -C₅ haloalkynyl, C₂ -C₇ alkoxyalkyl, (C₁ -C₃) alkoxy (C₁ -C₇) carbonylalkyl, C₂ -C₇ alkylthioalkyl; C₃ -C₆ cycloalkyl which may be substituted with C₁ -C₄ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; C₄ -C₉ cycloalkylalkyl which may be substituted with C₁ -C₄ alkyl; C₅ -C₆ cycloalkenyl which may be substituted with C₁ -C₄ alkyl; C₆ -C₈ cycloalkenylalkyl which may be substituted with C₁ -C₄ alkyl; or Q₁, Q₂, Q₃, Q₄, Q₅, Q₆, Q₇, Q₈, Q₉ or Q₁₀ of the general formula: ##STR203## wherein R⁴ and R¹² are independently halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy,R⁵ and R⁶ are independently hydrogen, C₁ -C₃ alkyl, trifluoromethyl or halogen, R⁷ is hydrogen or C₁ -C₃ alkyl, R⁸ is hydrogen, halogen or methyl, R⁹ is halogen, cyano, nitro, hydroxy, pentafluorosulfanyl(F₅ S), C₁ -C₈ alkyl, C₁ -C₃ haloalkyl, C₁ -C₈ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio, C₃ -C₆ alkenyloxy, C₃ -C₆ haloalkenyloxy, C₁ -C₃ hydroxyalkyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl, C₂ -C₄ alkynyloxy, C₂ -C₄ haloalkynyl, C₂ -C₄ haloalkynyloxy, C₂ -C₄ alkoxyalkyl, C₂ -C₄ alkylthioalkyl, C₃ -C₆ cycloalkyl, C₅ -C₆ cycloalkenyl, C₂ -C₅ alkoxycarbonyl, C₃ -C₆ cycloalkyloxy, C₅ -C₆ cycloalkenyloxy; phenyl which may be substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, C₃ -C₆ alkenyloxy or C₃ -C₆ haloalkenyloxy; phenoxy which may be substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, C₃ -C₆ alkenyloxy or C₃ -C₆ haloalkenyloxy; benzyl which may be substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, C₃ -C₆ alkenyloxy or C₃ -C₆ haloalkenyloxy; benzyloxy which may be substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, C₃ -C₆ alkenyloxy or C₃ -C₆ haloalkenyloxy; or pyridyloxy which may be substituted with halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, C₃ -C₆ alkenyloxy or C₃ -C₆ haloalkenyloxy; or when l is an integer of 2 to 5, two adjacent R⁹ 's are taken together to form trimethylene, tetramethylene, methylenedioxy which may be substituted with halogen or C₁ -C₃ alkyl; or ethylenedioxy which may be substituted with halogen or C₁ -C₃ alkyl, R¹⁰, R¹¹, R¹⁵ and R¹⁶ are independently hydrogen, C₁ -C₃ alkyl or trifluoromethyl, A is oxygen, S(O)_(t), NR¹³, C(═G¹)G² or G¹ C(═G²) wherein G¹ and G² are independently oxygen or sulfur, R¹³ is hydrogen, acetyl or C₁ -C₃ alkyl, and t is an integer of 0 to 2, Z¹ is oxygen, sulfur or NR¹⁷ wherein R¹⁷ is hydrogen, acetyl or C₁ -C₃ alkyl, l is an integer of 0 to 5, m is an integer of 0 to 4, n is an integer of 1 or 2, p is an integer of 0 to 6, q is an integer of 0 to 3, and s is an integer of 1 to 6; R², R³ and R¹⁴ are independently halogen, C₁ -C₃ haloalkyl or C₁ -C₃ alkyl, r is an integer of 0 to 2, X's are independently chlorine or bromine, Y is oxygen, NH or sulfur, and Z is oxygen, sulfur or NR¹³ wherein R¹³ is hydrogen, acetyl or C₁ -C₃ alkyl.
 2. The dihalopropene compound according to claim 1, wherein R² and R³ are independently halogen or C₁ -C₃ alkyl, and r is
 0. 3. The dihalopropene compound according to claim 1, wherein R² and R³ are independently chlorine, bromine, methyl, ethyl or isopropyl, and r is
 0. 4. The dihalopropene compound according to claim 1, wherein R² and R³ are both chlorine, and r is
 0. 5. The dihalopropene compound according to claim 1, wherein R² is chlorine, and R³ is methyl, and r is
 0. 6. The dihalopropene compound according to claim 1, wherein R² is ethyl, and R³ is methyl, and r is
 0. 7. The dihalopropene compound according to claim 1, wherein R² and R³ are both bromine and r is
 0. 8. The dihalopropene compound according to claim 1, wherein R² and R³ are both ethyl, and r is
 0. 9. The dihalopropene compound according to claim 1, wherein R² and R³ are independent halogen or C₁ -C₃ alkyl, r is 1 or 2, and R¹⁴ is halogen or C₁ -C₃ alkyl.
 10. The dihalopropene compound according to claim 1, wherein R² and R³ are independently halogen or C₁ -C₃ alkyl, r is 1 or 2, and R¹⁴ is halogen.
 11. The dihalopropene compound according to claim 1, wherein Y and Z are both oxygen.
 12. The dihalopropene compound according to claim 2, wherein Y and Z are both oxygen.
 13. The dihalopropene compound according to claim 1, wherein R¹ is Q₃.
 14. The dihalopropene compound according to claim 1, wherein R¹ is Q₃, p is 0, and R⁹ is halogen, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₃ haloalkoxy, C₁ -C₃ alkylthio, C₁ -C₃ haloalkylthio, cyano, nitro, or 3,4-methylenedioxy.
 15. The dihalopropene compound according to claim 1, wherein R¹ is Q₃ p is 0, and R⁹ is phenyl which may be substituted with halogen, pentafluorosulfanyl, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; benzyl which may be substituted with halogen, pentafluorosulfanyl, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; phenoxy which may be substituted with halogen, pentafluorosulfanyl, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; or benzyloxy which may be substituted with halogen, pentafluorosulfanyl, C₁ -C₄ alkyl, C₁ -C₃ haloalkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy.
 16. The dihalopropene compound according to claim 1, wherein R¹ is Q₃, p is 1 to 3, R¹⁰ and R¹¹ are both hydrogen, and R⁹ is halogen, trifluoromethyl, pentafluorosulfanyl or C₁ -C₃ haloalkoxy.
 17. The dihalopropene compound according to claim 12, wherein R¹ is Q₃, p is 1 to 3, R¹⁰ and R¹¹ are both hydrogen, and R⁹ is halogen, trifluoromethyl, pentafluorosulfanyl or C₁ -C₃ haloalkoxy.
 18. The dihalopropene compound according to claim 1, wherein R¹ is Q₅.
 19. The dihalopropene compound according to claim 1, wherein R¹ is Q₅, p is 1 to 4, R¹⁰ and R¹¹ both hydrogen, and R⁹ is halogen, trifluoromethyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkoxy, difluoromethylenedioxy or pentafluorosulfanyl.
 20. The dihalopropene compound according to claim 11, wherein R¹ is Q₅ p is 2 or 3, R¹⁰ and R¹¹ are both hydrogen, R⁹ is halogen, trifluoromethyl, isopropyloxy, C₁ -C₃ haloalkoxy, pentafluorosulfanyl or difluoromethylenedioxy, and A is oxygen.
 21. The dihalopropene compound according to claim 11, wherein R¹ is Q₅, p is 2 or 3, R¹⁰ and R¹¹ are both hydrogen, R⁹ is halogen, trifluoromethyl, isopropyloxy or C₁ -C₃ haloalkoxy, and A is oxygen.
 22. The dihalopropene compound according to claim 12, wherein R¹ is Q₂.
 23. The dihalopropene compound according to claim 12, wherein R¹ is Q₆.
 24. The dihalopropene compound according to claim 12, wherein R¹ is Q₁.
 25. The dihalopropene compound according to claim 12, wherein R¹ is Q₄.
 26. The dihalopropene compound according to claim 12, wherein R¹ is Q₇.
 27. The dihalopropene compound according to claim 12, wherein R¹ is Q₈.
 28. The dihalopropene compound according to claim 12, wherein R¹ is Q₉.
 29. The dihalopropene compound according to claim 12, wherein R¹ is Q₁₀.
 30. The dihalopropene compound according to claim 1, wherein R¹ is C₁ -C₁₀ alkyl, C₁ -C₅ haloalkyl, C₂ -C₁₀ alkenyl, C₂ -C₆ haloalkenyl, C₃ -C₉ alkynyl, C₃ -C₅ haloalkynyl, C₂ -C₇ alkoxyalkyl, (C₁ -C₃) alkoxy (C₁ -C₇) carbonylalkyl, C₂ -C₇ alkylthioalkyl; C₃ -C₆ cycloalkyl which may be substituted with C₁ -C₄ alkyl, C₁ -C₃ alkoxy or C₁ -C₃ haloalkoxy; C₄ -C₉ cycloalkylalkyl which may be substituted with C₁ -C₄ alkyl; C₅ -C₆ cycloalkenyl which may be substituted with C₁ -C₄ alkyl; or C₆ -C₈ cycloalkenylalkyl which may be substituted with C₁ -C₄ alkyl.
 31. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(3-(4-chlorophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 32. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(3-(4-bromophenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 33. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(3-(4-trifluoromethoxy)phenoxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 34. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(3-(4-trifluoromethylphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 35. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(3-(4-isopropyloxyphenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 36. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(3-(4-(1,1,2,2-tetrafluoroethoxy)phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 37. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(4-(4-chlorophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 38. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(4-(4-bromophenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 39. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(4-(4-trifluoromethoxy)phenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 40. The dihalopropene compound according to claim 1 which is 3, 5-Dichloro-4-(4-(4-trifluoromethylphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 41. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(4-(4-isopropyloxyphenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 42. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(4-(4-(1,1,2,2-tetrafluoroethoxy)phenoxy)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benezene.
 43. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(2-(4-bromophenyl)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 44. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(4-(4-chlorophenyl)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 45. The dihalopropene compound according to claim 1 which is 3,5-Dichloro-4-(4-(4-trifluoromethoxy)phenyl)butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 46. The dihalopropene compound according to claim 1 which is 3-Chloro-5-methyl-4-(3-(4-(trifluoromethoxy) phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 47. The dihalopropene compound according to claim 1 which is 3-Chloro-5-methyl-4-(3-(4-(trifluoromethyl) phenoxy) propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 48. ) The dihalopropene compound according to claim 1 which is 3-Ethyl-5-methyl-4-(3-(4-(trifluoromethoxy) phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 49. The dihalopropene compound according to claim 1 which is 3-Ethyl-5-methyl-4-(3-(4-(trifluoromethyl) phenoxy)propyloxy-1-(3,3-dichloro-2-propenyloxy)benzene.
 50. The dihalopropene compound according to claim 1 which is 3,5-Diethyl-4-(3-(4-(trifluoromethoxy) phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 51. The dihalopropene compound according to claim 1 which is 3,5-Diethyl-4-(3-(4-(trifluoromethyl)phenoxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 52. An insecticidal/acaricidal agent comprising the dihalopropene compound according to claim 1 as an active ingredient.
 53. A compound of the general formula: ##STR204## wherein R² and R³ are independently halogen, C₁ -C₃ alkyl or C₁ -C₃ haloalkyl, R⁷ is hydrogen or C₁ -C₃ alkyl, R¹⁰ and R¹¹ are independently hydrogen, C₁ -C₃ alkyl or trifluoromethyl X's are independently chlorine or bromine, L¹ is hydroxy, halogen, methanesulfonyloxy or p-toluenesulfonyloxy, and e is an integer of 2 to
 4. 54. A compound according to claim 53, wherein R⁷, R¹⁰ and R¹¹ are all hydrogen, and e is 2 or
 3. 55. The compound according to claim 53 which is 3,5-Dichloro-4-(3-chloropropyloxy)-1-(3,3-dichloro-2-propenyloxy) benzene.
 56. The compound according to claim 53 which is 3,5-Dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 57. The compound according to claim 53 which is 3,5-Dichloro-4-(4-chlorobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.
 58. The compound according to claim 53 which is 3,5-Dichloro-4(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy) benzene.
 59. The compound according to claim 53 which is 3,5-Dichloro-4-(3-hydroxypropyloxy)-1-(3,3-dichloro-2-propenyloxy) benzene.
 60. The compound according to claim 53 which is 3,5-Dichloro-4-(4-hydroxybutyloxy)-1-(3,3-dichloro-2-propenyloxy) benzene.
 61. A compound of the general formula: ##STR205## wherein R² and R³ are independently halogen, C₁ -C₃ -alkyl or C₁ -C₃ haloalkyl, and X's are independently chlorine or bromine.
 62. The compound according to claim 61 which is 2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenol.
 63. The compound according to claim 61 which is 2,6-Dichloro-4-(3,3-dibromo-2-propenyloxy)phenol.
 64. The compound according to claim 61 which is 2-Chloro-6-methyl-4-(3,3-dichloro-2-propenyloxy)phenol.
 65. The compound according to claim 61 which is 2-Chloro-6-methyl-4-(3,3-dibromo-2-propenyloxy)phenol.
 66. The compound according to claim 61 which is 2-Ethyl-6-meth -4-(3,3-dichloro-2-propenyloxy)phenol.
 67. The compound according to claim 61 which is 2-Ethyl-6-methyl-4-(3,3-dibromo-2-propenyloxy)phenol.
 68. A compound of the general formula: ##STR206## wherein R²¹ and R²² are independently halogen or C₁ -C₃ alkyl, R¹⁹ is halogen, C₁ -C₃ haloalkoxy or trifluoromethyl, u is 1 to 4, and l is an integer of 0 to
 5. 69. The compound according to claim 68 which is 3,5-Dichloro-4-(2-(4-bromophenyl)ethoxy)phenol.
 70. The compound according to claim 68 which is 3,5-Dichloro-4-(4-(4-chlorophenyl)butoxy)phenol.
 71. The compound according to claim 68 which is 3,5-Dichloro-4-(4(4-trifluoromethoxyphenyl)butoxy)phenol.
 72. A compound f the general formula: ##STR207## wherein R² and R³ are independently halogen, C₁ -C₃ alkyl or C₁ -C₃ haloalkyl, R⁷ is hydrogen or C₁ -C₃ alkyl, R¹⁰ and R¹¹ are independently hydrogen, C₁ -C₃ alkyl or trifluoromethyl, R²⁰ is halogen, C₁ -C₃ alkoxy, trifluoromethyl or C₁ -C₃ haloalkoxy, l is an integer of 0 to 5, e is an integer of 1 to 4, and B is oxygen, S(O)_(t) or NR¹³ wherein R¹³ is hydrogen, acetyl or C₁ -C₃ alkyl, and t is an integer of 0 to
 2. 73. The compound according to claim 72, wherein B is oxygen.
 74. The compound according to claim 72, wherein R² and R ³ are independently halogen or C₁ -C₃ alkyl, R⁷, R¹⁰ and R¹¹ are hydrogen, and e is an integer of 2 or
 3. 75. The compound according to claim 72, which is 3,5-Dichloro-4-(4-chlorophenoxy)propyloxy)phenol.
 76. The compound according to claim 72, which is 3,5-Dichloro-4-3-(4-bromophenoxy)propyloxy)phenol.
 77. The compound according to claim 72, which is 3,5-Dichloro- n3-(4-trifluoromethylphenoxy)propyloxy)phenol.
 78. The compound according to claim 72, which is 3,5-Dichloro-4-(3-(4-trifluoromethoxyphenoxy)propyloxy)phenol.
 79. The compound according to claim 72, which is 3,5-Dichloro-4-(3-(4-isopropoxyphenoxy)propyloxy)phenol.
 80. The compound according to claim 72, which is 3,5-Dichloro-4-(3-(4-(1,1,2,2-tetrafluoroethoxy)phenoxy) propyloxy)phenol.
 81. The compound according to claim 72, which is 3,5-Dichloro-4-(4(4-chlorophenoxy)butoxy)phenol.
 82. The compound according to claim 72, which is 3,5-Dichloro-4-(4(4-bromophenoxy)butoxy)phenol.
 83. The compound according to claim 72, which is 3,5-Dichloro-4-(4-(4-trifluoromethylphenoxy)butoxy)phenol.
 84. The compound according to claim 72, which is 3,5-Dichloro-4-(4-(4-trifluoromethoxyphenoxy)butoxy)phenol.
 85. The compound according to claim 72, which is 3,5-Dichloro-4-(4-isopropoxyphenoxy)butoxy)phenol.
 86. The compound according to claim 72, which is 3,5-Dichloro-4-(4-(4-(1,1,2,2-tetrafluoroethoxy)phenoxy) butoxy)phenol.
 87. The compound according to claim 72, which is 3-Chloro-5-methyl-4-(3-(4-(trifluoromethoxy)phenoxy)propyloxy)phenol.
 88. The compound according to claim 72, which is 3-Chloro-5-methyl-4-(3-(4-(trifluoromethyl)phenoxy)propyloxy)phenol.
 89. The compound according to claim 72, which is 3-Ethyl-4-(3-(4-trifluoromethoxy)phenoxy)propyloxy)phenol.
 90. The compound according to claim 72, which is 3-Ethyl-5-methyl-4-(3-(4-trifluoromethyl)phenoxy)propyloxy)phenol.
 91. The compound according to claim 72, which is 3,5-Diethyl-4t3-(4-(trifluoromethoxy)phenoxy)propyloxy)phenol.
 92. The compound according to claim 72, which is 3,5-Diethyl-4-(3-(4-(trifluoromethyl)phenoxy)propyloxy)phenol. 